$90+ Cheap flights from Cleveland (CLE) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — CHI
Jul 13 — Jul 201
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chicago are usually found in August or May, booked 76 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from Cleveland to Chicago
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Best
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Cheapest flights from Cleveland to ChicagoExplore the most affordable flight options available from Cleveland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 13, 2026.
Explore the most affordable flight options available from Cleveland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 13, 2026.
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:15 pm
CLE
- MDW
2 stops9h 35m
Southwest
Sat 8/157:40 am
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/12![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:35 pm
CLE
- MDW
1 stop5h 25m
Southwest
Wed 10/286:15 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/11![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:30 am
CLE
- ORD
Nonstop1h 37m
United Airlines
Wed 9/238:45 am
ORD
- CLE
Nonstop1h 42m
United Airlines
Deal found 6/12![United Airlines logo]()
$174
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:08 pm
CLE
- ORD
Nonstop1h 40m
United Airlines
Mon 9/77:20 am
ORD
- CLE
Nonstop1h 30m
United Airlines
Deal found 6/9![United Airlines logo]()
$176
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:25 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Wed 8/58:35 am
MDW
- CLE
Nonstop1h 25m
Southwest
Deal found 6/10![Southwest logo]()
$177
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:49 am
CLE
- ORD
Nonstop1h 36m
American Airlines
Tue 11/33:57 pm
ORD
- CLE
Nonstop1h 26m
American Airlines
Deal found 6/10![American Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:15 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Tue 11/31:55 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/8![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:05 pm
CLE
- ORD
Nonstop1h 36m
United Airlines
Wed 8/510:29 am
ORD
- CLE
Nonstop1h 29m
United Airlines
Deal found 6/12![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:00 am
CLE
- MDW
Nonstop1h 15m
Southwest
Tue 7/76:15 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/11![Southwest logo]()
$182
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:47 pm
CLE
- ORD
Nonstop1h 43m
American Airlines
Tue 7/711:30 am
ORD
- CLE
Nonstop1h 32m
American Airlines
Deal found 6/11![American Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:43 am
CLE
- MDW
1 stop3h 34m
Delta
Sat 8/299:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 6/12![Delta logo]()
$186
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:09 pm
CLE
- ORD
1 stop5h 21m
Delta
Sat 9/127:05 am
ORD
- CLE
1 stop5h 35m
Delta
Deal found 6/13![Delta logo]()
$186
Best flights from Cleveland to ChicagoDiscover carefully curated flight deals from Cleveland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 13, 2026.
Discover carefully curated flight deals from Cleveland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 13, 2026.
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:52 am
CLE
- ORD
Nonstop1h 37m
United Airlines
Fri 8/1410:43 am
ORD
- CLE
Nonstop1h 31m
United Airlines
Deal found 6/12![United Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:45 am
CLE
- RFD
1 stop27h 52m
Multiple Airlines
Sun 8/211:27 am
RFD
- CLE
1 stop10h 30m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:50 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Fri 8/142:35 pm
MDW
- CLE
2 stops6h 20m
Southwest
Deal found 6/12![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:18 am
CLE
- ORD
1 stop5h 50m
Delta
Thu 9/107:10 am
ORD
- CLE
1 stop5h 24m
Delta
Deal found 6/9![Delta logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/14:05 pm
CLE
- RFD
1 stop19h 32m
Multiple Airlines
Thu 8/611:37 am
RFD
- CLE
1 stop10h 20m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$215
This KAYAK deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:47 pm
CLE
- ORD
Nonstop1h 44m
American Airlines
Tue 7/216:38 am
ORD
- CLE
Nonstop1h 33m
American Airlines
Deal found 6/9![American Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:25 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Sun 8/308:05 am
MDW
- CLE
Nonstop1h 20m
Southwest
Deal found 6/9![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:30 am
CLE
- ORD
Nonstop1h 37m
United Airlines
Sun 8/304:15 pm
ORD
- CLE
Nonstop1h 32m
United Airlines
Deal found 6/12![United Airlines logo]()
$236
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:40 am
CLE
- MDW
1 stop4h 20m
Southwest
Wed 7/226:15 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/10![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:18 am
CLE
- MDW
1 stop5h 21m
Delta
Sun 8/239:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 6/8![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/289:47 pm
CLE
- RFD
1 stop12h 26m
Multiple Airlines
Thu 7/3011:27 am
RFD
- CLE
1 stop10h 30m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:45 am
CLE
- RFD
1 stop27h 52m
Multiple Airlines
Mon 8/37:50 pm
RFD
- CLE
1 stop11h 06m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$250
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/223:15 pm
CLE
- MDW
1 stop6h 15m
Southwest
Sun 8/308:50 am
MDW
- CLE
2 stops7h 10m
Southwest
Deal found 6/12![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:50 pm
CLE
- ORD
1 stop3h 39m
Delta
Sun 7/197:17 pm
ORD
- CLE
1 stop3h 39m
Delta
Deal found 6/12![Delta logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:05 pm
CLE
- RFD
1 stop19h 42m
Multiple Airlines
Mon 8/176:26 pm
RFD
- CLE
1 stop12h 12m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:05 pm
CLE
- ORD
Nonstop1h 39m
United Airlines
Thu 7/1610:29 am
ORD
- CLE
Nonstop1h 29m
United Airlines
Deal found 6/11![United Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/31:10 pm
CLE
- MDW
1 stop5h 40m
Southwest
Sun 7/56:10 am
MDW
- CLE
1 stop5h 25m
Southwest
Deal found 6/12![Southwest logo]()
$268
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
CLE
- ORD
Nonstop1h 40m
United Airlines
Sun 7/510:29 am
ORD
- CLE
Nonstop1h 29m
United Airlines
Deal found 6/11![United Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:20 pm
CLE
- MDW
1 stop3h 35m
Southwest
Sun 8/168:05 am
MDW
- CLE
Nonstop1h 20m
Southwest
Deal found 6/10![Southwest logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:00 am
CLE
- ORD
Nonstop1h 36m
United Airlines
Sun 7/127:25 am
ORD
- CLE
Nonstop1h 29m
United Airlines
Deal found 6/12![United Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:55 am
CLE
- MDW
Nonstop1h 15m
Southwest
Sun 8/28:00 am
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/9![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:20 pm
CLE
- RFD
1 stop14h 29m
Multiple Airlines
Sun 8/211:27 am
RFD
- CLE
1 stop10h 30m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1812:30 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Mon 7/2012:15 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 6/11![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:26 am
CLE
- ORD
2 stops8h 42m
Delta
Mon 8/315:20 pm
ORD
- CLE
1 stop3h 02m
Delta
Deal found 6/10![Delta logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/289:47 pm
CLE
- RFD
1 stop12h 26m
Multiple Airlines
Mon 8/37:50 pm
RFD
- CLE
1 stop11h 06m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:33 pm
CLE
- RFD
1 stop14h 16m
Multiple Airlines
Mon 8/106:26 pm
RFD
- CLE
2 stops16h 58m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:50 am
CLE
- MDW
2 stops7h 45m
Southwest
Sat 8/11:35 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 6/10![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:50 am
CLE
- MDW
2 stops7h 45m
Southwest
Sun 8/28:00 am
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/10![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:00 pm
CLE
- ORD
1 stop5h 31m
Delta
Thu 7/98:27 am
ORD
- CLE
2 stops9h 09m
Delta
Deal found 6/8![Delta logo]()
$473
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:05 pm
CLE
- ORD
Nonstop1h 36m
United Airlines
Fri 6/265:50 pm
ORD
- CLE
Nonstop1h 28m
United Airlines
Deal found 6/8![United Airlines logo]()
$434
Last-minute flights from Cleveland to ChicagoDiscover last-minute flight deals from Cleveland to Chicago. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Chicago. Data last updated June 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:47 pm
CLE
- ORD
Nonstop1h 43m
American Airlines
Tue 7/711:30 am
ORD
- CLE
Nonstop1h 32m
American Airlines
Deal found 6/11![American Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:18 am
CLE
- ORD
1 stop5h 46m
Delta
Tue 7/77:17 pm
ORD
- CLE
1 stop3h 39m
Delta
Deal found 6/11![Delta logo]()
$202
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:18 am
CLE
- MDW
1 stop5h 28m
Delta
Fri 7/36:58 pm
MDW
- CLE
1 stop4h 01m
Delta
Deal found 6/11![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:40 am
CLE
- MDW
1 stop4h 20m
Southwest
Wed 7/81:40 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 6/11![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:00 am
CLE
- MDW
Nonstop1h 15m
Southwest
Tue 7/76:15 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/11![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:30 am
CLE
- MDW
1 stop3h 44m
Delta
Tue 7/79:19 am
MDW
- CLE
1 stop3h 21m
Delta
Deal found 6/11![Delta logo]()
$202
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 pm
CLE
- ORD
Nonstop1h 54m
American Airlines
Fri 7/177:24 pm
ORD
- CLE
Nonstop1h 31m
American Airlines
Deal found 6/12![American Airlines logo]()
$193
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:45 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Tue 7/216:15 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/12![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:10 pm
CLE
- MDW
Nonstop1h 25m
Southwest
Tue 8/116:05 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 6/11![Southwest logo]()
$203
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
CLE
- ORD
Nonstop1h 36m
United Airlines
Tue 8/1110:43 am
ORD
- CLE
Nonstop1h 31m
United Airlines
Deal found 6/11![United Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:45 am
CLE
- RFD
1 stop27h 52m
Multiple Airlines
Sun 8/211:27 am
RFD
- CLE
1 stop10h 30m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:45 am
CLE
- RFD
1 stop27h 52m
Multiple Airlines
Thu 8/611:37 am
RFD
- CLE
1 stop10h 20m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$198
One-way flights from Cleveland to ChicagoSearch for one-way flight options from Cleveland to Chicago. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
Search for one-way flight options from Cleveland to Chicago. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:25 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Deal found 6/8![Southwest logo]()
$90
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:35 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Deal found 6/12![Southwest logo]()
$98
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:15 am
CLE
- ORD
Nonstop1h 31m
American Airlines
Deal found 6/13![American Airlines logo]()
$98
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:20 pm
CLE
- MDW
1 stop5h 13m
Delta
Deal found 6/8![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:18 am
CLE
- ORD
1 stop5h 50m
Delta
Deal found 6/8![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:43 am
CLE
- MDW
1 stop3h 34m
Delta
Deal found 6/11![Delta logo]()
$100
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:43 am
CLE
- ORD
1 stop4h 59m
Delta
Deal found 6/11![Delta logo]()
$100
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:04 am
CLE
- ORD
Nonstop1h 26m
American Airlines
Deal found 6/9![American Airlines logo]()
$104
This Priceline deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:46 pm
CLE
- MDW
1 stop7h 17m
Frontier
Deal found 6/12![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:22 pm
CLE
- ORD
1 stop10h 15m
Frontier
Deal found 6/10![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:45 am
CLE
- ORD
1 stop29h 30m
Frontier
Deal found 6/12![Frontier logo]()
$107
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/84:35 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Deal found 6/8![Southwest logo]()
$108
Find flight deals from Cleveland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $167 (Southwest) |
One-way from | $90 (Southwest) |
Popular in | January |
Cheapest in | August |
Average price | $277 |
Good round-trip deal | $252 or less |
Good one-way deal | $215 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Cleveland to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 13, 2026.
Use the filters below to find and compare flights from Cleveland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Tue 8/11
10:52 am-11:29 am
Nonstop1h 37m
Chicago O'Hare Intl
Fri 8/14
10:43 am-1:14 pm
Nonstop1h 31m
$193
ClevelandChicago
CLE - RFD
CLERFD
Cleveland Hopkins Intl
Wed 7/29
7:45 am-10:37 am
1 stop27h 52m
Chicago Greater Rockford
Sun 8/2
11:27 am-10:57 pm
1 stop10h 30m
$194
ClevelandChicago
CLE - RFD
CLERFD
Cleveland Hopkins Intl
Sat 8/1
4:05 pm-10:37 am
1 stop19h 32m
Chicago Greater Rockford
Thu 8/6
11:37 am-10:57 pm
1 stop10h 20m
$215
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 8/11
12:50 pm-1:05 pm
Nonstop1h 15m
Chicago Midway
Fri 8/14
2:35 pm-9:55 pm
2 stops6h 20m
$218
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 8/12
5:25 pm-5:40 pm
Nonstop1h 15m
Chicago Midway
Sun 8/30
8:05 am-10:25 am
Nonstop1h 20m
$227
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Mon 8/31
8:18 am-1:08 pm
1 stop5h 50m
Chicago O'Hare Intl
Thu 9/10
7:10 am-1:34 pm
1 stop5h 24m
$235
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Sat 8/22
5:30 am-6:07 am
Nonstop1h 37m
Chicago O'Hare Intl
Sun 8/30
4:15 pm-6:47 pm
Nonstop1h 32m
$236
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 7/22
10:40 am-2:00 pm
1 stop4h 20m
Chicago Midway
Wed 7/22
6:15 pm-8:30 pm
Nonstop1h 15m
$237
ClevelandChicago
CLE - RFD
CLERFD
Cleveland Hopkins Intl
Tue 7/28
9:47 pm-9:13 am
1 stop12h 26m
Chicago Greater Rockford
Thu 7/30
11:27 am-10:57 pm
1 stop10h 30m
$248
ClevelandChicago
CLE - RFD
CLERFD
Cleveland Hopkins Intl
Wed 7/29
7:45 am-10:37 am
1 stop27h 52m
Chicago Greater Rockford
Mon 8/3
7:50 pm-7:56 am
1 stop11h 06m
$250
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Cleveland to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cleveland to Chicago in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Cleveland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cleveland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cleveland-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Cleveland-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cleveland-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Cleveland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Cleveland with our price prediction graph.
CLE-CHI
CLE-MDW
CLE-ORD
CLE-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Cleveland to Chicago
CLE-CHI
CLE-MDW
CLE-ORD
CLE-RFD
What is the cheapest month to book a flight from Cleveland to Chicago?
Currently, May is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $83). Flying from Cleveland to Chicago in February is currently the most expensive (average of $128). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CLE to CHI?
Find hourly flight availability from Cleveland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 13, 2026.
A simple way to save on the total cost of your ticket is to fly from Cleveland to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight at noon.
Weekly flight availability from Cleveland to Chicago
Explore weekly flight availability from Cleveland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 13, 2026.
The most flights from CLE to CHI are scheduled on a Friday (66 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (51 on average).
How much does it cost to fly round-trip from Cleveland to Chicago?
How far ahead should I book a flight from Cleveland to Chicago?
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Cleveland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Cleveland to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Cleveland to Chicago. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Cleveland to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Cleveland to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Cleveland to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 13, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Cleveland to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Cleveland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 13, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Cleveland to Chicago by cabin class
Find flights from Cleveland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Cleveland and Chicago flights
Browse other Cleveland and Chicago flight options. Last updated on June 13, 2026.
Other flights from Cleveland
Browse through other flights departing from Cleveland. Flights are based on user searches made on Cheapflights and were last updated on June 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Cleveland to Chicago
Discover the top 4 airlines that operate flights from Cleveland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$107 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$127 | Average$266 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$139 | Average$270 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$146 | Average$315 | FlexibilityNo cancel fee | On-time69% |