$59+ Cheap flights from Cleveland (CLE) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — CHI
Oct 6 — Oct 131
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 May or March, booked 78 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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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 September 6, 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 September 6, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 10/77:25 pm -
Nonstop1h 15m
Thu 10/82:35 pm -
Nonstop1h 10m
Deal found 9/3![Southwest logo]()
$117
This United Airlines deal was found by Cheapflights users on 9/2. 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 9/245:20 am -
Nonstop1h 37m
Sat 9/2612:55 pm -
Nonstop1h 28m
Deal found 9/2![United Airlines logo]()
$117
This Priceline deal was found by Cheapflights users on 9/2. 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.
Thu 9/243:45 pm -
1 stop8h 59m
Sat 9/266:25 am -
1 stop4h 57m
Deal found 9/2![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 9/2. 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.
Tue 9/297:00 pm -
1 stop11h 38m
Tue 10/63:50 pm -
1 stop7h 40m
Deal found 9/2![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 9/2. 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.
Thu 9/247:00 am -
1 stop12h 23m
Mon 9/283:50 pm -
1 stop16h 17m
Deal found 9/2![Frontier logo]()
$119
This Southwest deal was found by Cheapflights users on 9/2. 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 10/19:00 pm -
1 stop3h 55m
Sat 10/38:25 am -
Nonstop1h 15m
Deal found 9/2![Southwest logo]()
$127
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:23 pm -
1 stop8h 18m
Mon 9/283:50 pm -
1 stop16h 17m
Deal found 9/2![Frontier logo]()
$128
This Trip.com deal was found by Cheapflights users on 9/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
1 stop12h 23m
Wed 9/303:50 pm -
1 stop7h 40m
Deal found 9/3![Frontier logo]()
$130
This Southwest deal was found by Cheapflights users on 9/2. 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 9/295:25 pm -
Nonstop1h 15m
Wed 9/3012:45 pm -
2 stops7h 20m
Deal found 9/2![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 9/2. 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 10/28:20 pm -
Nonstop1h 15m
Mon 10/52:35 pm -
Nonstop1h 10m
Deal found 9/2![Southwest logo]()
$134
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/27:00 am -
Nonstop1h 37m
Mon 10/59:30 pm -
Nonstop1h 29m
Deal found 9/2![United Airlines logo]()
$134
This Frontier deal was found by Cheapflights users on 9/2. 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.
Fri 10/303:46 pm -
1 stop9h 01m
Sat 11/147:25 am -
1 stop5h 09m
Deal found 9/2![Frontier logo]()
$135
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 September 6, 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 September 6, 2026.
This Southwest deal was found by Cheapflights users on 8/31. 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 9/245:25 pm -
Nonstop1h 15m
Mon 9/286:30 pm -
Nonstop1h 20m
Deal found 8/31![Southwest logo]()
$117
This United Airlines deal was found by Cheapflights users on 9/2. 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 9/245:20 am -
Nonstop1h 37m
Sat 9/2612:55 pm -
Nonstop1h 28m
Deal found 9/2![United Airlines logo]()
$117
This Delta deal was found by Cheapflights users on 9/2. 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 10/264:07 pm -
1 stop3h 22m
Wed 10/289:59 am -
1 stop6h 44m
Deal found 9/2![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 9/2. 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 10/77:25 pm -
Nonstop1h 15m
Wed 10/146:00 pm -
Nonstop1h 20m
Deal found 9/2![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/303:45 pm -
2 stops17h 55m
Wed 10/79:34 am -
1 stop13h 56m
Deal found 9/2![Multiple Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 9/1. 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 11/27:55 pm -
Nonstop1h 35m
Thu 11/57:50 am -
Nonstop1h 20m
Deal found 9/1![Southwest logo]()
$117
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/167:00 am -
Nonstop1h 37m
Tue 10/207:15 am -
Nonstop1h 26m
Deal found 9/1![United Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 9/2. 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 10/128:20 pm -
Nonstop1h 15m
Tue 10/132:45 pm -
1 stop5h 30m
Deal found 9/2![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 9/3. 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 11/68:10 pm -
1 stop3h 30m
Mon 11/912:55 pm -
2 stops6h 20m
Deal found 9/3![Southwest logo]()
$159
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Mon 9/286:10 pm -
Nonstop1h 40m
Fri 10/99:30 pm -
Nonstop1h 29m
Deal found 9/1![United Airlines logo]()
$204
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Mon 10/194:23 pm -
Nonstop1h 39m
Mon 10/199:30 pm -
Nonstop1h 29m
Deal found 9/2![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 9/1. 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 11/43:50 pm -
1 stop6h 35m
Fri 11/2712:50 pm -
Nonstop1h 10m
Deal found 9/1![Southwest logo]()
$183
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Sun 10/189:00 am -
Nonstop1h 37m
Wed 10/2112:55 pm -
Nonstop1h 28m
Deal found 9/3![United Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 10/209:59 pm -
1 stop11h 45m
Fri 10/237:56 pm -
1 stop25h 03m
Deal found 9/2![Multiple Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 9/249:59 pm -
1 stop11h 53m
Mon 9/284:50 pm -
1 stop22h 33m
Deal found 9/1![Multiple Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/27:00 am -
Nonstop1h 37m
Sun 10/49:04 am -
Nonstop1h 41m
Deal found 9/2![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 9/3. 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 10/82:40 pm -
Nonstop1h 15m
Sun 10/117:50 am -
Nonstop1h 15m
Deal found 9/3![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 9/2. 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 10/187:30 am -
Nonstop1h 20m
Wed 10/216:00 pm -
Nonstop1h 20m
Deal found 9/2![Southwest logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/279:59 pm -
1 stop11h 45m
Sun 11/110:20 am -
1 stop8h 43m
Deal found 9/3![Multiple Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/5. 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 9/2612:26 pm -
Nonstop1h 44m
Mon 9/2812:55 pm -
Nonstop1h 28m
Deal found 9/5![United Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 10/173:46 pm -
2 stops18h 54m
Wed 10/219:34 am -
1 stop13h 45m
Deal found 9/2![Multiple Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 9/3. 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 11/1312:35 pm -
Nonstop1h 15m
Sun 11/155:05 am -
1 stop5h 50m
Deal found 9/3![Southwest logo]()
$239
This United Airlines deal was found by Cheapflights users on 9/3. 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 11/66:00 am -
1 stop4h 45m
Mon 11/97:15 am -
Nonstop1h 26m
Deal found 9/3![United Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 10/56:00 am -
1 stop12h 41m
Wed 10/79:34 am -
1 stop13h 56m
Deal found 9/1![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 9/3. 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 10/94:50 pm -
1 stop3h 25m
Sun 10/117:50 am -
Nonstop1h 15m
Deal found 9/3![Southwest logo]()
$239
This United Airlines deal was found by Cheapflights users on 9/3. 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 11/144:23 pm -
Nonstop1h 46m
Sun 11/157:00 am -
1 stop4h 48m
Deal found 9/3![United Airlines logo]()
$263
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/72:57 pm -
1 stop4h 44m
Wed 10/147:15 am -
Nonstop1h 26m
Deal found 9/1![United Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 9/4. 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 10/158:20 pm -
Nonstop1h 15m
Tue 10/202:45 pm -
2 stops5h 20m
Deal found 9/4![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 9/1. 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 9/267:15 am -
1 stop3h 15m
Sun 9/273:25 pm -
Nonstop1h 10m
Deal found 9/1![Southwest logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/56:00 am -
1 stop12h 41m
Fri 10/98:02 pm -
1 stop24h 57m
Deal found 9/3![Multiple Airlines logo]()
$426
Last-minute flights from Cleveland to ChicagoDiscover last-minute flight deals from Cleveland to Chicago. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Chicago. Data last updated September 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/2. 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 9/245:20 am -
Nonstop1h 37m
Sat 9/2612:55 pm -
Nonstop1h 28m
Deal found 9/2![United Airlines logo]()
$117
This Priceline deal was found by Cheapflights users on 9/2. 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.
Thu 9/243:45 pm -
1 stop8h 59m
Sat 9/266:25 am -
1 stop4h 57m
Deal found 9/2![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 9/2. 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.
Thu 9/247:00 am -
1 stop12h 23m
Mon 9/283:50 pm -
1 stop16h 17m
Deal found 9/2![Frontier logo]()
$119
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:23 pm -
1 stop8h 18m
Mon 9/283:50 pm -
1 stop16h 17m
Deal found 9/2![Frontier logo]()
$128
This Trip.com deal was found by Cheapflights users on 9/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
1 stop12h 23m
Wed 9/303:50 pm -
1 stop7h 40m
Deal found 9/3![Frontier logo]()
$130
This Expedia deal was found by Cheapflights users on 9/2. 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.
Tue 9/296:00 am -
1 stop17h 59m
Wed 9/303:50 pm -
1 stop16h 17m
Deal found 9/2![Frontier logo]()
$118
This CheapOair deal was found by Cheapflights users on 9/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop17h 59m
Tue 10/63:50 pm -
1 stop7h 40m
Deal found 9/1![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 9/2. 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 9/295:25 pm -
Nonstop1h 15m
Wed 9/3012:45 pm -
2 stops7h 20m
Deal found 9/2![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 9/2. 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 10/19:00 pm -
1 stop3h 55m
Sat 10/38:25 am -
Nonstop1h 15m
Deal found 9/2![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 9/2. 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 10/28:20 pm -
Nonstop1h 15m
Mon 10/52:35 pm -
Nonstop1h 10m
Deal found 9/2![Southwest logo]()
$134
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/27:00 am -
Nonstop1h 37m
Mon 10/59:30 pm -
Nonstop1h 29m
Deal found 9/2![United Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 9/2. 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 10/77:25 pm -
Nonstop1h 15m
Wed 10/146:00 pm -
Nonstop1h 20m
Deal found 9/2![Southwest logo]()
$117
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 September 6, 2026.
Search for one-way flight options from Cleveland to Chicago. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This Southwest deal was found by Cheapflights users on 9/2. 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 9/297:15 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$59
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Mon 10/55:20 am -
Nonstop1h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![United Airlines logo]()
$59
This Frontier deal was found by Cheapflights users on 9/3. 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.
Sat 10/107:51 am -
1 stop8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$60
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
1 stop11h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$64
This Super.com deal was found by Cheapflights users on 9/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
1 stop12h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$64
This Expedia deal was found by Cheapflights users on 9/1. 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.
Thu 10/17:00 am -
1 stop11h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$65
This Frontier deal was found by Cheapflights users on 9/2. 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.
Thu 10/11:35 pm -
1 stop10h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$65
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
1 stop11h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$66
This Southwest deal was found by Cheapflights users on 9/3. 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 10/296:00 am -
2 stops7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$74
This Southwest deal was found by Cheapflights users on 9/2. 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 10/28:20 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$76
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/26:06 pm -
Nonstop1h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$76
This Delta deal was found by Cheapflights users on 9/1. 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 9/296:30 am -
1 stop3h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Delta logo]()
$79
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 September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | January |
Cheapest in | May |
Average price | $240 |
Good round-trip deal | $283 or less |
Good one-way deal | $176 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 7,457,451 searches. Data last updated September 6, 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
Quickest round-trip
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 9/29
7:15 pm-7:30 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Mon 10/5
5:20 am-5:57 am
Nonstop1h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 10/6
8:35 am-8:55 am
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Wed 9/30
6:10 pm-6:50 pm
Nonstop1h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 12/1
6:05 pm-9:30 pm
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$69
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Mon 3/1
6:25 am-1:45 pm
2 stops8h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$74
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Thu 2/11
5:50 am-1:30 pm
1 stop8h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$74
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Fri 10/9
8:20 pm-8:35 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$76
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Wed 3/3
10:10 am-12:33 pm
1 stop3h 23m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Wed 10/7
8:10 am-12:59 pm
1 stop5h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
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 September.
| 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 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 $251). Flying from Cleveland to Chicago in January is currently the most expensive (average of $365). 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 September 6, 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 September 6, 2026.
The most flights from CLE to CHI are scheduled on a Friday (70 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Cleveland to Chicago?
Airfare is below average for this route at the moment.
Cleveland to Chicago flights typically cost between $183 and $375 in October.The cheapest round-trip price found within the last 5 days was $117 on Southwest (Oct 7-Oct 14).
How far ahead should I book a flight from Cleveland to Chicago?
Booking 53 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 August 29, 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.
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 September 6, 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.
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
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 September 6, 2026.
Complete your trip
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Cleveland and Chicago flights
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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 September 6, 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 7,457,451 searches. Data last updated September 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$267 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$135 | Average$318 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$264 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$143 | Average$201 | FlexibilityNo cancel fee | On-time62% |