$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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — CHI
Oct 22 — Oct 291
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 22, 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 22, 2026.
This Southwest deal was found by Cheapflights users on 9/20. 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 10/176:40 pm -
1 stop4h 05m
Mon 10/197:45 am -
Nonstop1h 15m
Deal found 9/20![Southwest logo]()
$127
This CheapOair deal was found by Cheapflights users on 9/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:59 pm -
1 stop10h 32m
Tue 10/208:46 am -
1 stop14h 33m
Deal found 9/20![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 9/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:59 pm -
1 stop10h 32m
Wed 10/289:51 am -
1 stop25h 45m
Deal found 9/21![Frontier logo]()
$130
This Southwest deal was found by Cheapflights users on 9/21. 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.
Mon 10/262:40 pm -
Nonstop1h 15m
Tue 10/272:45 pm -
2 stops5h 20m
Deal found 9/21![Southwest logo]()
$132
This Frontier deal was found by Cheapflights users on 9/20. 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 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 9/20![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 9/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:59 pm -
1 stop11h 47m
Sat 11/147:15 am -
1 stop5h 19m
Deal found 9/20![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 9/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:20 pm -
1 stop19h 11m
Mon 10/128:11 pm -
1 stop11h 46m
Deal found 9/19![Frontier logo]()
$136
This Southwest deal was found by Cheapflights users on 9/22. 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.
Wed 10/1410:10 am -
1 stop6h 55m
Thu 10/155:00 am -
1 stop6h 00m
Deal found 9/22![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 9/21. 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.
Thu 10/158:20 am -
Nonstop1h 20m
Mon 10/196:45 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$144
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Fri 10/167:00 am -
Nonstop1h 37m
Tue 10/207:15 am -
Nonstop1h 26m
Deal found 9/21![United Airlines logo]()
$144
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:57 pm -
1 stop6h 40m
Mon 12/76:10 am -
1 stop17h 31m
Deal found 9/19![Frontier logo]()
$145
This CheapOair deal was found by Cheapflights users on 9/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:33 pm -
1 stop11h 53m
Mon 10/268:11 pm -
1 stop11h 55m
Deal found 9/22![Frontier logo]()
$148
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 22, 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 22, 2026.
This Southwest deal was found by Cheapflights users on 9/20. 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 10/175:25 pm -
Nonstop1h 20m
Tue 10/202:10 pm -
1 stop5h 55m
Deal found 9/20![Southwest logo]()
$127
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:42 pm -
Nonstop1h 48m
Fri 10/307:49 pm -
Nonstop1h 26m
Deal found 9/18![United Airlines logo]()
$144
This Delta deal was found by Cheapflights users on 9/22. 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.
Sat 12/124:10 pm -
1 stop5h 05m
Mon 12/1412:34 pm -
1 stop5h 40m
Deal found 9/22![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 9/20. 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.
Fri 10/169:00 pm -
1 stop3h 55m
Sat 10/178:25 am -
Nonstop1h 15m
Deal found 9/20![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 10/178:10 am -
1 stop5h 49m
Mon 10/193:30 pm -
1 stop7h 00m
Deal found 9/18![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 9/22. 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.
Sat 2/67:00 am -
1 stop5h 42m
Sat 2/65:45 pm -
1 stop3h 56m
Deal found 9/22![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 9/18. 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.
Wed 10/284:20 pm -
1 stop6h 05m
Fri 10/3011:00 am -
1 stop5h 10m
Deal found 9/18![Southwest logo]()
$164
This Delta deal was found by Cheapflights users on 9/21. 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.
Sat 12/56:10 am -
1 stop5h 19m
Mon 12/77:15 pm -
1 stop3h 44m
Deal found 9/21![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:50 pm -
Nonstop1h 48m
Thu 10/297:15 am -
Nonstop1h 26m
Deal found 9/18![United Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 9/17. 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 10/88:20 pm -
Nonstop1h 15m
Mon 11/97:50 am -
Nonstop1h 20m
Deal found 9/17![Southwest logo]()
$183
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:20 am -
Nonstop1h 37m
Sun 10/188:05 pm -
Nonstop1h 31m
Deal found 9/18![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 9/22. 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 10/155:50 pm -
1 stop5h 10m
Mon 10/196:45 pm -
Nonstop1h 15m
Deal found 9/22![Southwest logo]()
$193
This United Airlines deal was found by Cheapflights users on 9/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/299:40 pm -
Nonstop1h 46m
Thu 12/39:50 pm -
Nonstop1h 24m
Deal found 9/22![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 9/20. 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.
Mon 10/264:07 pm -
1 stop3h 22m
Wed 10/289:59 am -
1 stop6h 44m
Deal found 9/20![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:20 am -
Nonstop1h 20m
Mon 10/266:25 pm -
1 stop4h 25m
Deal found 9/19![Southwest logo]()
$193
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:49 pm -
Nonstop1h 40m
Tue 11/312:55 pm -
Nonstop1h 28m
Deal found 9/18![United Airlines logo]()
$234
This Southwest deal was found by Cheapflights users on 9/21. 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.
Fri 10/169:00 pm -
1 stop3h 55m
Sun 10/257:50 am -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 10/158:20 am -
Nonstop1h 20m
Sun 10/185:10 am -
1 stop5h 35m
Deal found 9/18![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 9/18. 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.
Fri 11/208:35 am -
Nonstop1h 25m
Mon 11/237:50 am -
Nonstop1h 20m
Deal found 9/18![Southwest logo]()
$288
Last-minute flights from Cleveland to ChicagoDiscover last-minute flight deals from Cleveland to Chicago. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Chicago. Data last updated September 22, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 9/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:20 pm -
1 stop19h 11m
Mon 10/128:11 pm -
1 stop11h 46m
Deal found 9/19![Frontier logo]()
$136
This Southwest deal was found by Cheapflights users on 9/22. 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.
Wed 10/1410:10 am -
1 stop6h 55m
Thu 10/155:00 am -
1 stop6h 00m
Deal found 9/22![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 9/21. 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.
Thu 10/158:20 am -
Nonstop1h 20m
Mon 10/196:45 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$144
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Fri 10/167:00 am -
Nonstop1h 37m
Tue 10/207:15 am -
Nonstop1h 26m
Deal found 9/21![United Airlines logo]()
$144
This CheapOair deal was found by Cheapflights users on 9/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:39 pm -
1 stop14h 12m
Tue 10/208:46 am -
1 stop14h 33m
Deal found 9/22![Frontier logo]()
$145
This Southwest deal was found by Cheapflights users on 9/20. 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 10/176:40 pm -
1 stop4h 05m
Mon 10/197:45 am -
Nonstop1h 15m
Deal found 9/20![Southwest logo]()
$127
This CheapOair deal was found by Cheapflights users on 9/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:59 pm -
1 stop10h 32m
Tue 10/208:46 am -
1 stop14h 33m
Deal found 9/20![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 9/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:59 pm -
1 stop10h 32m
Wed 10/289:51 am -
1 stop25h 45m
Deal found 9/21![Frontier logo]()
$130
This CheapOair deal was found by Cheapflights users on 9/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:33 pm -
1 stop11h 53m
Mon 10/268:11 pm -
1 stop11h 55m
Deal found 9/22![Frontier logo]()
$148
This Southwest deal was found by Cheapflights users on 9/21. 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.
Mon 10/262:40 pm -
Nonstop1h 15m
Tue 10/272:45 pm -
2 stops5h 20m
Deal found 9/21![Southwest logo]()
$132
This Frontier deal was found by Cheapflights users on 9/19. 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 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 9/19![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 9/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:59 pm -
1 stop11h 47m
Sat 11/147:15 am -
1 stop5h 19m
Deal found 9/20![Frontier logo]()
$135
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 22, 2026.
Search for one-way flight options from Cleveland to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/22. 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 10/202:20 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$59
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:45 pm -
Nonstop1h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$59
This CheapOair deal was found by Cheapflights users on 9/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/274:50 pm -
1 stop8h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$60
This Super.com deal was found by Cheapflights users on 9/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:46 pm -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$64
This Super.com deal was found by Cheapflights users on 9/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:59 pm -
1 stop10h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$64
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/263:46 pm -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Thu 10/157:00 am -
1 stop11h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 9/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:11 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$76
This Delta deal was found by Cheapflights users on 9/22. 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.
Tue 10/206:10 am -
1 stop4h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 9/18. 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.
Wed 12/164:00 pm -
1 stop3h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 9/21. 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.
Sat 10/176:20 am -
2 stops9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$80
This Super.com deal was found by Cheapflights users on 9/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:46 pm -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$81
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 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | January |
Cheapest in | May |
Average price | $246 |
Good round-trip deal | $314 or less |
Good one-way deal | $201 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 22, 2026.
Use the filters below to find and compare flights from Cleveland to Chicago that are best for you.
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Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Mon 11/9
12:35 pm-12:50 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 11/23
6:00 am-6:38 am
Nonstop1h 38m
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
Thu 10/15
8:20 am-8:40 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
Mon 11/2
7:50 pm-8:38 pm
Nonstop1h 48m
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 11/3
7:10 pm-7:35 pm
Nonstop1h 25m
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
Thu 10/15
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
Thu 11/5
12:35 pm-12:50 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
Sat 10/31
4:19 pm-5:05 pm
Nonstop1h 46m
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
Thu 11/19
1:55 pm-2:30 pm
Nonstop1h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Mon 11/2
7:55 pm-8:30 pm
Nonstop1h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
Showing 1-10 of 41 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 Accuracy- | Trust Score*1 star |
- 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
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
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 22, 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 26% 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 22, 2026.
The most flights from CLE to CHI are scheduled on a Monday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 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 $197 and $342 in October.The cheapest round-trip price found within the last 5 days was $127 on Southwest (Oct 17-Oct 19).
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 September 19, 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 22, 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.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
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 22, 2026.
Complete your trip
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Search flights from Cleveland to Chicago by cabin class
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Cleveland and Chicago flights
Browse other Cleveland and Chicago flight options. Last updated on September 22, 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 September 22, 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$266 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$134 | Average$259 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$136 | Average$323 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$146 | Average$222 | FlexibilityNo cancel fee | On-time62% |