$76+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — CHI
May 23 — May 301
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 86 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Cleveland to Chicago
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Best
Last-minute
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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 April 23, 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 April 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/113:49 pm
CLE
- MDW
1 stop20h 20m
Frontier
Wed 5/1312:04 pm
MDW
- CLE
1 stop5h 23m
Frontier
Deal found 4/18![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/187:24 pm
CLE
- ORD
1 stop13h 31m
Frontier
Wed 5/276:55 am
ORD
- CLE
1 stop6h 36m
Frontier
Deal found 4/20![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/137:24 pm
CLE
- MDW
1 stop16h 45m
Frontier
Wed 5/206:00 am
MDW
- CLE
1 stop25h 36m
Frontier
Deal found 4/20![Frontier logo]()
$147
This Orbitz deal was found by Cheapflights users on 4/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:42 pm
CLE
- ORD
1 stop9h 17m
Frontier
Sun 5/178:39 am
ORD
- CLE
1 stop11h 46m
Frontier
Deal found 4/20![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/163:49 pm
CLE
- MDW
1 stop7h 13m
Frontier
Sun 5/246:00 am
MDW
- CLE
1 stop12h 34m
Frontier
Deal found 4/20![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Fri 5/157:24 pm
CLE
- ORD
1 stop13h 31m
Frontier
Sun 5/246:55 am
ORD
- CLE
1 stop11h 39m
Frontier
Deal found 4/20![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Fri 6/57:24 pm
CLE
- MDW
1 stop27h 38m
Frontier
Tue 6/912:27 pm
MDW
- CLE
1 stop7h 28m
Frontier
Deal found 4/20![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/163:49 pm
CLE
- MDW
1 stop7h 13m
Frontier
Mon 5/186:00 am
MDW
- CLE
1 stop11h 27m
Frontier
Deal found 4/20![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/126:01 pm
CLE
- ORD
1 stop14h 54m
Frontier
Mon 5/186:55 am
ORD
- CLE
1 stop24h 58m
Frontier
Deal found 4/19![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/146:54 am
CLE
- MDW
1 stop16h 08m
Frontier
Sat 5/1611:59 am
MDW
- CLE
1 stop5h 28m
Frontier
Deal found 4/18![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/117:24 pm
CLE
- ORD
1 stop13h 31m
Frontier
Sat 5/161:59 pm
ORD
- CLE
1 stop17h 54m
Frontier
Deal found 4/20![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 6/33:36 pm
CLE
- MDW
1 stop7h 26m
Frontier
Thu 6/116:00 am
MDW
- CLE
1 stop13h 55m
Frontier
Deal found 4/20![Frontier logo]()
$159
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 April 23, 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 April 23, 2026.
This Southwest deal was found by Cheapflights users on 4/22. 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 5/196:45 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Tue 5/264:40 pm
MDW
- CLE
1 stop3h 35m
Southwest
Deal found 4/22![Southwest logo]()
$188
This Delta deal was found by Cheapflights users on 4/22. 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 5/134:00 pm
CLE
- MDW
1 stop3h 33m
Delta
Wed 5/206:23 am
MDW
- CLE
1 stop5h 40m
Delta
Deal found 4/22![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 6/104:05 pm
CLE
- RFD
1 stop19h 32m
Multiple Airlines
Fri 6/127:53 pm
RFD
- CLE
1 stop11h 04m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 4/21. 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 7/257:01 am
CLE
- ORD
Nonstop1h 36m
United Airlines
Sun 8/210:30 am
ORD
- CLE
Nonstop1h 29m
United Airlines
Deal found 4/21![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 4/23. 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 5/266:45 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Sat 5/307:40 am
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 4/23![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 4/22. 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 6/312:45 pm
CLE
- ORD
2 stops8h 29m
Delta
Wed 6/106:30 am
ORD
- CLE
2 stops6h 16m
Delta
Deal found 4/22![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 4/20. 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 9/107:15 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Mon 9/214:25 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 4/20![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 4/22. 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 8/124:25 pm
CLE
- MDW
1 stop6h 21m
Delta
Fri 8/145:25 pm
MDW
- CLE
1 stop4h 42m
Delta
Deal found 4/22![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 4/22. 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 6/49:20 pm
CLE
- MDW
1 stop3h 55m
Southwest
Mon 6/85:25 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 4/22![Southwest logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Fri 5/85:30 am
CLE
- RFD
1 stop13h 49m
Multiple Airlines
Mon 5/117:09 pm
RFD
- CLE
1 stop18h 06m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sun 8/97:20 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Wed 8/1212:35 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 4/21![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 4/21. 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 5/206:35 am
CLE
- ORD
1 stop4h 54m
Delta
Sun 5/247:00 am
ORD
- CLE
2 stops7h 15m
Delta
Deal found 4/21![Delta logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/67:24 pm
CLE
- RFD
2 stops15h 23m
Multiple Airlines
Sun 5/1010:37 am
RFD
- CLE
1 stop11h 03m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 6/29:57 pm
CLE
- RFD
1 stop12h 20m
Multiple Airlines
Fri 6/57:53 pm
RFD
- CLE
1 stop11h 07m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 4/21. 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 8/272:05 pm
CLE
- ORD
1 stop3h 31m
Delta
Sun 8/306:00 am
ORD
- CLE
2 stops6h 34m
Delta
Deal found 4/21![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 4/20. 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 5/234:50 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Mon 5/257:55 am
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 4/20![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 4/22. 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 8/2012:00 pm
CLE
- ORD
2 stops7h 41m
Delta
Sun 8/231:35 pm
ORD
- CLE
1 stop4h 45m
Delta
Deal found 4/22![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 4/21. 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 5/136:40 am
CLE
- MDW
2 stops10h 05m
Southwest
Wed 5/2010:10 am
MDW
- CLE
2 stops5h 50m
Southwest
Deal found 4/21![Southwest logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Fri 5/229:57 pm
CLE
- RFD
1 stop12h 24m
Multiple Airlines
Sun 5/2411:27 am
RFD
- CLE
1 stop10h 13m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 4/21. 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 5/296:00 am
CLE
- ORD
2 stops8h 01m
Delta
Sun 5/315:30 am
ORD
- CLE
1 stop5h 06m
Delta
Deal found 4/21![Delta logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Sun 5/109:57 pm
CLE
- RFD
1 stop13h 02m
Multiple Airlines
Wed 5/1312:09 pm
RFD
- CLE
1 stop11h 29m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 4/18. 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 5/183:45 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Tue 5/1912:45 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 4/18![Southwest logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/289:57 pm
CLE
- RFD
1 stop22h 16m
Multiple Airlines
Mon 6/18:03 pm
RFD
- CLE
1 stop10h 45m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 4/18. 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 6/128:18 am
CLE
- ORD
2 stops9h 44m
Delta
Sun 6/147:01 am
ORD
- CLE
1 stop5h 45m
Delta
Deal found 4/18![Delta logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 6/99:42 pm
CLE
- RFD
1 stop12h 35m
Multiple Airlines
Fri 6/127:53 pm
RFD
- CLE
1 stop11h 04m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 4/20. 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 5/236:00 am
CLE
- ORD
2 stops7h 56m
Delta
Sat 5/235:41 pm
ORD
- CLE
1 stop4h 29m
Delta
Deal found 4/20![Delta logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Fri 5/229:57 pm
CLE
- RFD
1 stop12h 24m
Multiple Airlines
Mon 5/258:03 pm
RFD
- CLE
1 stop10h 45m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 4/19. 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 5/217:42 pm
CLE
- ORD
1 stop5h 17m
Delta
Tue 5/267:00 am
ORD
- CLE
2 stops8h 28m
Delta
Deal found 4/19![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 4/18. 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 5/222:13 pm
CLE
- ORD
1 stop4h 52m
Delta
Sun 5/246:24 am
ORD
- CLE
2 stops7h 41m
Delta
Deal found 4/18![Delta logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Sun 5/317:55 am
CLE
- RFD
1 stop24h 50m
Multiple Airlines
Mon 6/297:48 pm
RFD
- CLE
1 stop11h 09m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$336
Last-minute flights from Cleveland to ChicagoDiscover last-minute flight deals from Cleveland to Chicago. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Chicago. Data last updated April 23, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:00 am
CLE
- MDW
1 stop8h 12m
Frontier
Fri 5/154:52 pm
MDW
- CLE
1 stop19h 17m
Frontier
Deal found 4/21![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/113:49 pm
CLE
- MDW
1 stop20h 20m
Frontier
Wed 5/1312:04 pm
MDW
- CLE
1 stop5h 23m
Frontier
Deal found 4/18![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/117:24 pm
CLE
- ORD
1 stop13h 31m
Frontier
Sat 5/161:59 pm
ORD
- CLE
1 stop17h 54m
Frontier
Deal found 4/20![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/126:01 pm
CLE
- ORD
1 stop14h 54m
Frontier
Mon 5/186:55 am
ORD
- CLE
1 stop24h 58m
Frontier
Deal found 4/19![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/137:24 pm
CLE
- MDW
1 stop16h 45m
Frontier
Wed 5/206:00 am
MDW
- CLE
1 stop25h 36m
Frontier
Deal found 4/20![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/146:54 am
CLE
- MDW
1 stop16h 08m
Frontier
Sat 5/1611:59 am
MDW
- CLE
1 stop5h 28m
Frontier
Deal found 4/18![Frontier logo]()
$156
This Orbitz deal was found by Cheapflights users on 4/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:42 pm
CLE
- ORD
1 stop9h 17m
Frontier
Sun 5/178:39 am
ORD
- CLE
1 stop11h 46m
Frontier
Deal found 4/20![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Fri 5/157:24 pm
CLE
- ORD
1 stop13h 31m
Frontier
Sun 5/246:55 am
ORD
- CLE
1 stop11h 39m
Frontier
Deal found 4/20![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/163:49 pm
CLE
- MDW
1 stop7h 13m
Frontier
Sun 5/246:00 am
MDW
- CLE
1 stop12h 34m
Frontier
Deal found 4/20![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/163:49 pm
CLE
- MDW
1 stop7h 13m
Frontier
Mon 5/186:00 am
MDW
- CLE
1 stop11h 27m
Frontier
Deal found 4/20![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/187:24 pm
CLE
- ORD
1 stop13h 31m
Frontier
Wed 5/276:55 am
ORD
- CLE
1 stop6h 36m
Frontier
Deal found 4/20![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/303:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Sat 6/66:00 am
MDW
- CLE
1 stop5h 32m
Frontier
Deal found 4/20![Frontier logo]()
$152
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 April 23, 2026.
Search for one-way flight options from Cleveland to Chicago. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/186:54 am
CLE
- MDW
1 stop29h 15m
Frontier
Deal found 4/20![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/196:01 pm
CLE
- ORD
1 stop14h 54m
Frontier
Deal found 4/20![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/137:24 pm
CLE
- MDW
1 stop16h 45m
Frontier
Deal found 4/20![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/187:24 pm
CLE
- ORD
1 stop13h 31m
Frontier
Deal found 4/21![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 8/115:51 pm
CLE
- MDW
1 stop29h 17m
Frontier
Deal found 4/22![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 8/103:46 pm
CLE
- ORD
1 stop17h 07m
Frontier
Deal found 4/22![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Fri 5/83:49 pm
CLE
- MDW
1 stop20h 15m
Frontier
Deal found 4/18![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Fri 5/87:24 pm
CLE
- ORD
1 stop25h 27m
Frontier
Deal found 4/18![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 7/216:40 am
CLE
- MDW
1 stop16h 31m
Frontier
Deal found 4/20![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 7/203:46 pm
CLE
- MDW
1 stop20h 26m
Frontier
Deal found 4/21![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 4/297:38 pm
CLE
- RFD
1 stop15h 09m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$88
This Southwest deal was found by Cheapflights users on 4/21. 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 5/206:45 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Deal found 4/21![Southwest logo]()
$89
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 April 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $145 (Kiwi.com) |
One-way from | $76 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $314 |
Good round-trip deal | $277 or less |
Good one-way deal | $189 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 April 23, 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 - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 5/19
6:45 pm-7:00 pm
Nonstop1h 15m
Chicago Midway
Tue 5/26
4:40 pm-9:15 pm
1 stop3h 35m
$188
Quickest round-trip
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 5/26
6:45 pm-7:00 pm
Nonstop1h 15m
Chicago Midway
Sat 5/30
7:40 am-9:50 am
Nonstop1h 10m
$196
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 5/13
4:00 pm-6:33 pm
1 stop3h 33m
Chicago Midway
Wed 5/20
6:23 am-1:03 pm
1 stop5h 40m
$197
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Wed 6/3
12:45 pm-8:14 pm
2 stops8h 29m
Chicago O'Hare Intl
Wed 6/10
6:30 am-1:46 pm
2 stops6h 16m
$208
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Thu 9/10
7:15 pm-7:30 pm
Nonstop1h 15m
Chicago Midway
Mon 9/21
4:25 pm-6:40 pm
Nonstop1h 15m
$216
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Thu 6/4
9:20 pm-12:15 am
1 stop3h 55m
Chicago Midway
Mon 6/8
5:25 pm-7:35 pm
Nonstop1h 10m
$225
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Sun 8/9
7:20 pm-7:35 pm
Nonstop1h 15m
Chicago Midway
Wed 8/12
12:35 pm-2:45 pm
Nonstop1h 10m
$227
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 8/12
4:25 pm-9:46 pm
1 stop6h 21m
Chicago Midway
Fri 8/14
5:25 pm-11:07 pm
1 stop4h 42m
$234
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Sat 5/23
4:50 pm-5:10 pm
Nonstop1h 20m
Chicago Midway
Mon 5/25
7:55 am-10:10 am
Nonstop1h 15m
$247
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Wed 5/20
6:35 am-10:29 am
1 stop4h 54m
Chicago O'Hare Intl
Sun 5/24
7:00 am-3:15 pm
2 stops7h 15m
$252
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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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
How far ahead should I book a flight from Cleveland to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Chicago. Price data was last updated on April 17, 2026.
Booking 86 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 month to book a flight from Cleveland to Chicago?
Currently, June is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $68). 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 April 23, 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 29% on your trip compared to booking a flight at noon.
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 April 18, 2026.
Travelers seeking maximum savings on their Cleveland to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 23, 2026.
The most flights from CLE to CHI are scheduled on a Monday (82 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).
How much does it cost to fly round-trip from Cleveland to Chicago?
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 April 23, 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.
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Cleveland to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 April 23, 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 April 23, 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 April 23, 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 April 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$127 | Average$267 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$137 | Average$262 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$143 | Average$297 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$143 | Average$194 | FlexibilityNo cancel fee | On-time62% |