HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$76+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 March or May, booked 68 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

Cheap flight deals from Rochester to Chicago

Cheapest flights from Rochester to Chicago
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 January 21, 2026.

This JetBlue deal was found by Cheapflights users on 1/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:07 am
ROC
-
ORD
1 stop8h 13m
JetBlue
Tue 5/123:15 pm
ORD
-
ROC
1 stop7h 24m
JetBlue
Deal found 1/21$205
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:20 pm
ROC
-
ORD
1 stop6h 17m
Multiple Airlines
Tue 3/35:58 pm
ORD
-
ROC
2 stops37h 47m
Multiple Airlines
Deal found 1/20$229
This Expedia deal was found by Cheapflights users on 1/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:10 am
ROC
-
ORD
1 stop6h 15m
JetBlue
Wed 3/2512:20 pm
ORD
-
ROC
1 stop10h 11m
JetBlue
Deal found 1/20$239
This JetBlue deal was found by Cheapflights users on 1/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:05 am
ROC
-
ORD
1 stop7h 15m
JetBlue
Fri 9/116:45 am
ORD
-
ROC
1 stop4h 40m
JetBlue
Deal found 1/19$245
This Southwest deal was found by Cheapflights users on 1/18. 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.
Sat 5/98:05 am
ROC
-
MDW
Nonstop1h 50m
Southwest
Sat 5/163:35 pm
MDW
-
ROC
Nonstop1h 30m
Southwest
Deal found 1/18$258
This lastminute.com deal was found by Cheapflights users on 1/20. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
ROC
-
ORD
1 stop18h 21m
JetBlue
Thu 2/2612:41 pm
ORD
-
ROC
1 stop19h 19m
JetBlue
Deal found 1/20$265
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/159:25 am
ROC
-
ORD
2 stops24h 00m
Multiple Airlines
Wed 3/258:41 pm
ORD
-
ROC
1 stop11h 42m
Multiple Airlines
Deal found 1/20$269
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/213:53 pm
ROC
-
ORD
1 stop8h 54m
Multiple Airlines
Tue 2/248:42 pm
ORD
-
ROC
2 stops35h 41m
Multiple Airlines
Deal found 1/20$273
This United Airlines deal was found by Cheapflights users on 1/20. 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 2/105:23 pm
ROC
-
ORD
Nonstop2h 26m
United Airlines
Wed 2/1110:35 am
ORD
-
ROC
Nonstop2h 04m
United Airlines
Deal found 1/20$277
This Expedia deal was found by Cheapflights users on 1/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:10 am
ROC
-
ORD
1 stop6h 15m
JetBlue
Wed 3/1812:20 pm
ORD
-
ROC
1 stop10h 11m
JetBlue
Deal found 1/19$284
This Expedia deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/96:30 am
ROC
-
ORD
2 stops12h 13m
JetBlue
Wed 2/117:40 am
ORD
-
ROC
2 stops14h 47m
JetBlue
Deal found 1/21$286
This Southwest deal was found by Cheapflights users on 1/18. 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.
Sat 2/283:15 pm
ROC
-
MDW
Nonstop2h 05m
Southwest
Mon 3/26:10 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 1/18$287

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$205
(JetBlue)

One-way from

$76
(Expedia)

Popular in

December

Cheapest in

March

Average price

$399

Good round-trip deal

$321 or less

Good one-way deal

$135 or less
Provider with most accurate pricing for Greater Rochester Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greater Rochester Intl-Chicago (CHI) flights.
Search Deals
From Greater Rochester Intl to Chicago (CHI)
Search Deals
One-way flight from Greater Rochester Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Greater Rochester Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Greater Rochester Intl to Chicago (CHI).
Search Deals

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 2,558,603 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Rochester to Chicago that are best for you.

Fly from

Rochester

Fly to

Chicago

Route

Depart

Return

Price

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 2/18

6:10 am-8:54 am

1 stop3h 44m

Chicago Midway

Wed 2/25

6:00 am-12:04 pm

1 stop5h 04m

$297

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 2/10

10:22 am-4:49 pm

1 stop7h 27m

Chicago O'Hare Intl

Thu 2/12

10:38 am-1:43 pm

Nonstop2h 05m

$306

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 2/10

3:40 pm-7:00 pm

1 stop4h 20m

Chicago Midway

Thu 2/12

11:10 am-1:45 pm

Nonstop1h 35m

$306

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Sat 5/9

6:05 am-3:30 pm

2 stops10h 25m

Chicago O'Hare Intl

Sat 5/16

6:00 am-2:45 pm

1 stop7h 45m

$311

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 2/18

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

Wed 2/25

2:20 pm-4:55 pm

Nonstop1h 35m

$312

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Wed 3/18

6:45 am-7:55 am

Nonstop2h 10m

Chicago O'Hare Intl

Wed 3/18

6:12 pm-9:03 pm

Nonstop1h 51m

$315

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Sat 5/9

6:30 am-7:37 am

Nonstop2h 07m

Chicago O'Hare Intl

Sat 5/16

1:55 pm-4:45 pm

Nonstop1h 50m

$315

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 2/19

6:20 am-7:30 am

Nonstop2h 10m

Chicago O'Hare Intl

Mon 2/23

6:15 pm-9:06 pm

Nonstop1h 51m

$315

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 2/21

3:15 pm-4:20 pm

Nonstop2h 05m

Chicago Midway

Thu 2/26

11:10 am-1:45 pm

Nonstop1h 35m

$315

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Sat 2/28

5:26 pm-6:35 pm

Nonstop2h 09m

Chicago O'Hare Intl

Mon 3/2

6:15 pm-9:06 pm

Nonstop1h 51m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 41 results
1
2
3
...
5

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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 Expedia the most. Expedia 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.
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

How far ahead should I book a flight from Rochester to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Rochester to Chicago. Price data was last updated on January 16, 2026.

To ensure you get the cheapest price possible for a flight from Rochester to Chicago, you should look to book at least 63 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 month to book a flight from Rochester to Chicago?

Currently, July is the cheapest month in which you can book a flight from Rochester to Chicago (average of $77). Flying from Rochester to Chicago in March is currently the most expensive (average of $217). 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 January 21, 2026.

It’s typically best to fly out from Rochester to Chicago in the afternoon. Doing so could potentially save you 19% on the flight price compared to flying at noon, which is usually more expensive.

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 January 17, 2026.

Travelers seeking maximum savings on their Rochester to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from 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 January 21, 2026.

The most flights from ROC to CHI are scheduled on a Monday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

How much does it cost to fly round-trip from Rochester to Chicago?

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 January 21, 2026.
See what other customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,089 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,191 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,174 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • What airport do you fly from for flights from Rochester to Chicago?

    Greater Rochester Intl (ROC), located 3.8 mi from the city center, is the airport you fly out of when you book flights from Rochester to Chicago. 3 airlines have flights from Greater Rochester Intl to Chicago on a regular basis. Booking flights from Greater Rochester Intl to Chicago should not be difficult; the airport handles an average of 18 outbound flights to Chicago per day.

  • How long is the flight from Rochester to Chicago?

    Delta, United Airlines, and Southwest can get you from Rochester to Chicago in just under 3h 44m. Your travel time can differ by up to 3h 43m. Rochester and Chicago are separated by a distance of 521 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Rochester to Chicago round-trip?

    Currently priced at $197, American Airlines will fly you from Rochester to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Southwest - these airlines can fly you to your destination from $240 and $303, respectively. American Airlines is priced at 45% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Rochester to Chicago?

    The top 3 most reliable airlines when flying from Rochester to Chicago are Envoy Air (75%), SkyWest Airlines (75%) and Qatar Airways (74%).

  • What are the cheapest flights from Rochester to Chicago?

    The cheapest flight price from Rochester to Chicago is $123. On average you can expect to pay $811. The most popular route, (Greater Rochester Intl - Chicago O'Hare Intl), can usually be booked for $239.

  • Can I find deals for flights from Rochester to Chicago that include hotel bookings?

    Yes. In addition to deals on Rochester to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Rochester to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Rochester to Chicago.

  • Can I find deals for business class flights from Rochester to Chicago?

    Yes. Cheapflights offers flight deals from Rochester to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Rochester to Chicago?

    Currently, July is the cheapest month in which you can book a flight from Rochester to Chicago (average of $77). Flying from Rochester to Chicago in March is currently the most expensive (average of $217). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Rochester to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Newark to St. Louis flights
LaGuardia to Midway flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Syracuse to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Albany to O'Hare Intl flights
Rochester to O'Hare Intl flights
White Plains to O'Hare Intl flights
Syracuse to Midway flights
Albany to Midway flights
Buffalo to Midway flights
Rochester to Midway flights
Islip to O'Hare Intl flights
White Plains to Midway flights
Syracuse to St. Louis flights
Albany to St. Louis flights
Ithaca to O'Hare Intl flights
Newark to Moline flights
Newark to Peoria flights
LaGuardia to Moline flights
LaGuardia to Peoria flights
Elmira to O'Hare Intl flights
Rochester to St. Louis flights
White Plains to St. Louis flights
Newark to Bloomington flights
John F Kennedy Intl to Moline flights
LaGuardia to Decatur flights
Newark to Evansville flights
John F Kennedy Intl to Bloomington flights
Buffalo to St. Louis flights
Elmira to Midway flights
Stewart to O'Hare Intl flights
Ithaca to Midway flights
John F Kennedy Intl to Peoria flights
John F Kennedy Intl to Evansville flights
LaGuardia to Evansville flights
Albany to Moline flights
Newark to Champaign flights
John F Kennedy Intl to Champaign flights
LaGuardia to Champaign flights
Islip to St. Louis flights
LaGuardia to Bloomington flights
Watertown to O'Hare Intl flights

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 2,558,603 searches. Data last updated January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$197Average$394FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$240Average$360FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$303Average$393FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.