$111+ Cheap flights from Rochester (ROC) 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Sep 25 — Oct 21
Round-trip
1 adult, Economy
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Find cheap flights from Rochester 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 Greater Rochester Intl to Chicago are usually found in April or August, booked 74 days in advance, depart on a Wednesday or Tuesday and return on a Saturday
Cheap flight deals from Rochester to Chicago
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Best
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Cheapest flights from Rochester to ChicagoExplore the most affordable flight options available from Rochester to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
Explore the most affordable flight options available from Rochester to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 9/156:22 am -
Nonstop2h 08m
Wed 9/166:30 am -
Nonstop2h 01m
Deal found 8/21![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 8/21. 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.
Tue 9/156:20 pm -
Nonstop1h 45m
Wed 9/168:30 am -
Nonstop1h 45m
Deal found 8/21![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/26. 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 10/55:40 pm -
Nonstop2h 08m
Thu 10/86:15 pm -
Nonstop1h 50m
Deal found 8/26![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 8/25. 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 9/236:20 pm -
Nonstop1h 45m
Sat 9/263:15 pm -
Nonstop1h 40m
Deal found 8/25![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:40 am -
Nonstop2h 20m
Mon 9/289:04 pm -
Nonstop1h 55m
Deal found 8/25![American Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Mon 9/145:52 pm -
Nonstop2h 08m
Fri 9/186:25 pm -
Nonstop2h 04m
Deal found 8/21![United Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 8/21. 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 9/146:45 pm -
Nonstop1h 50m
Fri 9/186:15 pm -
Nonstop1h 45m
Deal found 8/21![Southwest logo]()
$281
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:08 pm -
1 stop7h 28m
Mon 10/198:02 am -
Nonstop1h 53m
Deal found 8/24![American Airlines logo]()
$288
This United Airlines deal was found by Cheapflights users on 8/25. 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 10/281:08 pm -
Nonstop2h 21m
Fri 10/307:07 am -
Nonstop1h 55m
Deal found 8/25![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 8/24. 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 9/256:45 pm -
Nonstop1h 50m
Wed 9/308:30 am -
Nonstop1h 45m
Deal found 8/24![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/26. 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 9/236:05 am -
2 stops6h 45m
Wed 9/308:30 am -
Nonstop1h 45m
Deal found 8/26![Southwest logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/157:53 pm -
1 stop20h 43m
Thu 10/228:04 am -
1 stop10h 09m
Deal found 8/24![Multiple Airlines logo]()
$296
Best flights from Rochester to ChicagoDiscover carefully curated flight deals from Rochester to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
Discover carefully curated flight deals from Rochester to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 10/16:20 am -
Nonstop2h 08m
Mon 10/56:55 am -
Nonstop1h 59m
Deal found 8/21![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 8/21. 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 10/175:00 pm -
Nonstop1h 50m
Mon 10/195:00 am -
1 stop5h 50m
Deal found 8/21![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 8/21. 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 10/16:00 am -
1 stop5h 28m
Mon 10/55:10 pm -
1 stop4h 44m
Deal found 8/21![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 9/227:50 pm -
1 stop4h 50m
Thu 9/246:15 pm -
Nonstop1h 50m
Deal found 8/21![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 8/25. 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 9/236:20 pm -
Nonstop1h 45m
Sat 9/263:15 pm -
Nonstop1h 40m
Deal found 8/25![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 8/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:10 am -
1 stop4h 53m
Mon 10/266:44 pm -
1 stop3h 11m
Deal found 8/23![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/25. 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 10/266:10 am -
Nonstop2h 19m
Wed 10/287:07 am -
Nonstop1h 55m
Deal found 8/25![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 8/22. 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 11/188:05 am -
Nonstop2h 00m
Sat 11/2112:50 pm -
Nonstop1h 35m
Deal found 8/22![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 8/21. 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 10/2812:23 pm -
1 stop5h 03m
Fri 10/302:30 pm -
1 stop7h 36m
Deal found 8/21![Delta logo]()
$301
This United Airlines deal was found by Cheapflights users on 8/25. 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 10/281:08 pm -
Nonstop2h 21m
Fri 10/307:07 am -
Nonstop1h 55m
Deal found 8/25![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 8/21. 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 11/118:05 am -
Nonstop2h 00m
Sun 11/156:45 pm -
Nonstop1h 40m
Deal found 8/21![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 8/24. 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 10/56:00 am -
1 stop4h 07m
Thu 10/86:44 pm -
1 stop3h 11m
Deal found 8/24![Delta logo]()
$311
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:50 pm -
1 stop4h 50m
Sat 9/268:50 am -
1 stop4h 15m
Deal found 8/25![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 8/21. 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 10/1512:42 pm -
1 stop6h 18m
Sun 10/186:44 pm -
1 stop3h 11m
Deal found 8/21![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 8/22. 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.
Fri 10/3011:25 am -
2 stops8h 50m
Sun 11/112:55 pm -
Nonstop1h 35m
Deal found 8/22![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Sat 10/106:20 am -
Nonstop2h 08m
Mon 10/126:15 pm -
Nonstop1h 50m
Deal found 8/22![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/22. 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.
Fri 10/236:05 pm -
1 stop5h 12m
Sun 10/256:15 am -
1 stop4h 41m
Deal found 8/22![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 8/24. 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 9/247:55 pm -
1 stop4h 37m
Wed 9/306:55 am -
Nonstop1h 59m
Deal found 8/24![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 8/22. 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 11/186:00 am -
1 stop5h 39m
Sat 11/215:30 am -
1 stop4h 44m
Deal found 8/22![Delta logo]()
$369
Last-minute flights from Rochester to ChicagoDiscover last-minute flight deals from Rochester to Chicago. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Rochester to Chicago. Data last updated August 26, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Mon 9/145:52 pm -
Nonstop2h 08m
Fri 9/186:25 pm -
Nonstop2h 04m
Deal found 8/21![United Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 8/21. 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 9/146:45 pm -
Nonstop1h 50m
Fri 9/186:15 pm -
Nonstop1h 45m
Deal found 8/21![Southwest logo]()
$281
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 9/156:22 am -
Nonstop2h 08m
Wed 9/166:30 am -
Nonstop2h 01m
Deal found 8/21![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 8/21. 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.
Tue 9/156:20 pm -
Nonstop1h 45m
Wed 9/168:30 am -
Nonstop1h 45m
Deal found 8/21![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/25. 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 9/186:22 am -
Nonstop2h 08m
Mon 9/216:25 pm -
Nonstop2h 04m
Deal found 8/25![United Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:40 am -
Nonstop2h 20m
Mon 9/289:04 pm -
Nonstop1h 55m
Deal found 8/25![American Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 8/25. 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 9/225:30 am -
1 stop7h 55m
Thu 9/246:00 am -
1 stop4h 48m
Deal found 8/25![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:40 am -
Nonstop2h 20m
Wed 9/308:05 am -
Nonstop1h 57m
Deal found 8/26![American Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 8/26. 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 9/236:20 pm -
Nonstop1h 45m
Wed 9/308:30 am -
Nonstop1h 45m
Deal found 8/26![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am -
1 stop5h 46m
Sat 9/264:55 pm -
Nonstop2h 01m
Deal found 8/25![American Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 8/25. 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 9/236:05 am -
1 stop3h 55m
Sat 9/269:05 am -
Nonstop1h 40m
Deal found 8/25![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/24. 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 9/256:45 pm -
Nonstop1h 50m
Wed 9/308:30 am -
Nonstop1h 45m
Deal found 8/24![Southwest logo]()
$291
One-way flights from Rochester to ChicagoSearch for one-way flight options from Rochester to Chicago. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
Search for one-way flight options from Rochester to Chicago. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/237:05 pm -
2 stops20h 40m
Deal found 8/22![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/228:03 pm -
1 stop20h 33m
Deal found 8/22![Multiple Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 8/22. 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.
Sat 11/217:30 pm -
Nonstop2h 05m
Deal found 8/22![Southwest logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/217:05 pm -
2 stops21h 31m
Deal found 8/22![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 11/187:05 pm -
2 stops21h 32m
Deal found 8/22![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 11/208:15 pm -
1 stop29h 01m
Deal found 8/24![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/167:05 pm -
2 stops20h 40m
Deal found 8/25![Multiple Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 8/21. 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.
Tue 9/2212:27 pm -
1 stop4h 48m
Deal found 8/21![Delta logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/237:05 pm -
3 stops23h 41m
Deal found 8/22![Multiple Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 8/22. 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 10/65:55 am -
2 stops9h 30m
Deal found 8/22![Southwest logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 10/258:03 pm -
2 stops28h 40m
Deal found 8/25![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:05 pm -
3 stops23h 40m
Deal found 8/23![Multiple Airlines logo]()
$159
Find flight deals from Rochester to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Rochester (ROC) 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 August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (United Airlines) |
One-way from | $111 (Kiwi.com) |
Popular in | February |
Cheapest in | April |
Average price | $388 |
Good round-trip deal | $359 or less |
Good one-way deal | $173 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Rochester 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 August 26, 2026.
Use the filters below to find and compare flights from Rochester to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
RochesterChicago
ROC Greater Rochester Intl - ORD Chicago O'Hare Intl
ROCORD
Greater Rochester Intl
Thu 10/1
6:20 am-7:28 am
Nonstop2h 08m
Chicago O'Hare Intl
Mon 10/5
6:55 am-9:54 am
Nonstop1h 59m
$257
RochesterChicago
ROC Greater Rochester Intl - MDW Chicago Midway
ROCMDW
Greater Rochester Intl
Sat 10/17
5:00 pm-5:50 pm
Nonstop1h 50m
Chicago Midway
Mon 10/19
5:00 am-11:50 am
1 stop5h 50m
$267
RochesterChicago
ROC Greater Rochester Intl - ORD Chicago O'Hare Intl
ROCORD
Greater Rochester Intl
Tue 9/22
7:50 pm-11:40 pm
1 stop4h 50m
Chicago O'Hare Intl
Thu 9/24
6:15 pm-9:05 pm
Nonstop1h 50m
$267
RochesterChicago
ROC Greater Rochester Intl - ORD Chicago O'Hare Intl
ROCORD
Greater Rochester Intl
Thu 10/1
6:00 am-10:28 am
1 stop5h 28m
Chicago O'Hare Intl
Mon 10/5
5:10 pm-10:54 pm
1 stop4h 44m
$277
Quickest round-trip
RochesterChicago
ROC Greater Rochester Intl - MDW Chicago Midway
ROCMDW
Greater Rochester Intl
Wed 9/23
6:20 pm-7:05 pm
Nonstop1h 45m
Chicago Midway
Sat 9/26
3:15 pm-5:55 pm
Nonstop1h 40m
$277
RochesterChicago
ROC Greater Rochester Intl - ORD Chicago O'Hare Intl
ROCORD
Greater Rochester Intl
Mon 10/26
6:10 am-7:29 am
Nonstop2h 19m
Chicago O'Hare Intl
Wed 10/28
7:07 am-10:02 am
Nonstop1h 55m
$277
RochesterChicago
ROC Greater Rochester Intl - MDW Chicago Midway
ROCMDW
Greater Rochester Intl
Wed 11/18
8:05 am-9:05 am
Nonstop2h 00m
Chicago Midway
Sat 11/21
12:50 pm-3:25 pm
Nonstop1h 35m
$291
RochesterChicago
ROC Greater Rochester Intl - ORD Chicago O'Hare Intl
ROCORD
Greater Rochester Intl
Wed 10/28
1:08 pm-2:29 pm
Nonstop2h 21m
Chicago O'Hare Intl
Fri 10/30
7:07 am-10:02 am
Nonstop1h 55m
$291
RochesterChicago
ROC Greater Rochester Intl - MDW Chicago Midway
ROCMDW
Greater Rochester Intl
Thu 10/22
6:10 am-10:03 am
1 stop4h 53m
Chicago Midway
Mon 10/26
6:44 pm-10:55 pm
1 stop3h 11m
$297
RochesterChicago
ROC Greater Rochester Intl - MDW Chicago Midway
ROCMDW
Greater Rochester Intl
Wed 11/11
8:05 am-9:05 am
Nonstop2h 00m
Chicago Midway
Sun 11/15
6:45 pm-9:25 pm
Nonstop1h 40m
$297
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Rochester 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 Rochester to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Rochester-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Rochester-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Rochester-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Rochester-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 Rochester-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 Rochester to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Rochester with our price prediction graph.
ROC-CHI
ROC-ORD
ROC-MDW
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 Rochester to Chicago
ROC-CHI
ROC-ORD
ROC-MDW
What is the cheapest month to book a flight from Rochester to Chicago?
Currently, April is the cheapest month in which you can book a flight from Rochester to Chicago (average of $394). Flying from Rochester to Chicago in February is currently the most expensive (average of $481). 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 ROC to CHI?
Find hourly flight availability from Rochester 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 August 26, 2026.
It’s typically best to fly out from Rochester to Chicago in the afternoon. Doing so could potentially save you 52% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Rochester to Chicago
Explore weekly flight availability from Rochester 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 August 26, 2026.
The most flights from ROC to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Rochester to Chicago?
Airfare is below average for this route at the moment.
Rochester to Chicago flights typically cost between $334 and $475 in October.The cheapest round-trip price found within the last 5 days was $257 on United Airlines (Oct 1-Oct 5).
How far ahead should I book a flight from Rochester to Chicago?
To ensure you get the cheapest price possible for a flight from Rochester to Chicago, you should look to book at least 85 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Rochester to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Rochester to Chicago. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Rochester to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 August 26, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Rochester to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
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 Rochester 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
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Rochester and Chicago flights
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Other flights from Rochester
Browse through other flights departing from Rochester. Flights are based on user searches made on Cheapflights and were last updated on August 26, 2026.
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Top 3 airlines flying from Rochester to Chicago
Discover the top 3 airlines that operate flights from Rochester 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 August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$459 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$453 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$331 | Average$489 | FlexibilityNo cancel fee | On-time63% |