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$85+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
1 adult, Economy
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Cheapflights Tip: The best prices from Greater Rochester Intl to Chicago are usually found in September or April, booked 68 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 June 27, 2026.

This Southwest deal was found by Cheapflights users on 6/25. 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 7/294:25 pm
ROC
-
MDW
2 stops7h 50m
Southwest
Sun 8/29:05 am
MDW
-
ROC
1 stop7h 15m
Southwest
Deal found 6/25$374
This American Airlines deal was found by Cheapflights users on 6/26. 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.
Thu 7/305:43 pm
ROC
-
ORD
1 stop6h 47m
American Airlines
Tue 8/49:03 pm
ORD
-
ROC
Nonstop1h 53m
American Airlines
Deal found 6/26$376
This Southwest deal was found by Cheapflights users on 6/25. 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.
Thu 9/34:05 pm
ROC
-
MDW
1 stop4h 10m
Southwest
Sun 9/61:35 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 6/25$376
This Southwest deal was found by Cheapflights users on 6/25. 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.
Thu 8/612:55 pm
ROC
-
MDW
1 stop10h 45m
Southwest
Sun 8/95:10 am
MDW
-
ROC
1 stop6h 55m
Southwest
Deal found 6/25$377
This Delta deal was found by Cheapflights users on 6/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:15 pm
ROC
-
ORD
1 stop6h 42m
Delta
Sat 9/56:30 pm
ORD
-
ROC
2 stops15h 23m
Delta
Deal found 6/26$379
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:20 pm
ROC
-
MDW
2 stops8h 00m
Southwest
Sat 8/89:55 am
MDW
-
ROC
2 stops10h 05m
Southwest
Deal found 6/23$379
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Fri 7/176:05 am
ROC
-
ORD
1 stop7h 25m
American Airlines
Tue 7/215:58 am
ORD
-
ROC
1 stop4h 31m
American Airlines
Deal found 6/24$380
This Delta deal was found by Cheapflights users on 6/23. 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.
Wed 7/156:15 pm
ROC
-
MDW
1 stop5h 00m
Delta
Sat 7/189:19 am
MDW
-
ROC
1 stop5h 27m
Delta
Deal found 6/23$380
This Southwest deal was found by Cheapflights users on 6/22. 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 8/206:45 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Sun 8/238:50 am
MDW
-
ROC
2 stops8h 10m
Southwest
Deal found 6/22$381
This Southwest deal was found by Cheapflights users on 6/24. 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 8/712:55 pm
ROC
-
MDW
1 stop10h 45m
Southwest
Mon 8/108:10 am
MDW
-
ROC
Nonstop1h 45m
Southwest
Deal found 6/24$382
This United Airlines deal was found by Cheapflights users on 6/22. 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.
Tue 7/286:20 am
ROC
-
ORD
Nonstop2h 08m
United Airlines
Thu 8/66:45 am
ORD
-
ROC
Nonstop1h 52m
United Airlines
Deal found 6/22$384
This KAYAK deal was found by Cheapflights users on 6/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:26 pm
ROC
-
ORD
Nonstop2h 20m
American Airlines
Sun 9/204:55 pm
ORD
-
ROC
Nonstop2h 01m
American Airlines
Deal found 6/24$385

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 June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$374
(Southwest)

One-way from

$85
(JetBlue)

Popular in

June

Cheapest in

September

Average price

$481

Good round-trip deal

$393 or less

Good one-way deal

$238 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. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 27, 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

Price

Cheapest round-trip

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 9/1

6:15 pm-11:57 pm

1 stop6h 42m

Chicago O'Hare Intl

Sat 9/5

6:30 pm-10:53 am

2 stops15h 23m

$379

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 7/16

6:16 am-10:37 am

1 stop5h 21m

Chicago O'Hare Intl

Tue 7/21

6:00 am-11:57 am

1 stop4h 57m

$380

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 8/16

6:30 am-2:05 pm

2 stops8h 35m

Chicago Midway

Wed 8/19

6:30 am-12:15 pm

1 stop4h 45m

$385

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 9/15

6:00 am-12:16 pm

1 stop7h 16m

Chicago O'Hare Intl

Sun 9/20

4:55 pm-7:56 pm

Nonstop2h 01m

$395

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 7/28

6:00 am-10:05 am

1 stop5h 05m

Chicago Midway

Mon 8/3

6:42 pm-10:52 pm

1 stop3h 10m

$395

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 9/15

12:29 pm-4:30 pm

1 stop5h 01m

Chicago O'Hare Intl

Sun 9/20

5:30 am-11:34 am

1 stop5h 04m

$401

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 7/16

6:16 am-9:13 am

1 stop3h 57m

Chicago Midway

Sat 7/18

9:19 am-3:46 pm

1 stop5h 27m

$408

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 7/17

6:16 am-9:13 am

1 stop3h 57m

Chicago Midway

Sat 7/18

6:35 pm-10:47 pm

1 stop3h 12m

$408
Quickest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 7/28

7:05 pm-7:50 pm

Nonstop1h 45m

Chicago Midway

Mon 8/3

6:50 pm-9:30 pm

Nonstop1h 40m

$411

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 7/9

12:55 pm-5:10 pm

1 stop5h 15m

Chicago Midway

Wed 7/29

9:10 am-6:25 pm

2 stops8h 15m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 41 resultsSorted by cheapest first
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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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 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.
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

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

Currently, February is the cheapest month in which you can book a flight from Rochester to Chicago (average of $75). Flying from Rochester to Chicago in June is currently the most expensive (average of $293). 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 June 27, 2026.

It’s typically best to fly out from Rochester to Chicago in the afternoon. Doing so could potentially save you 33% 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 June 27, 2026.

The most flights from ROC to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).

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

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 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 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 June 20, 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 June 27, 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.
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,246 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,896 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,779 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 24 outbound flights to Chicago per day.

  • How long is the flight from Rochester to Chicago?

    Delta, Southwest, and American Airlines can get you from Rochester to Chicago in just under 6h 42m. Your travel time can differ by up to 1h 53m. Rochester and Chicago are separated by a distance of 526 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 $260, United Airlines will fly you from Rochester to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Southwest - these airlines can fly you to your destination from $283 and $305, respectively. United Airlines is priced at 37% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Rochester to Chicago one-way?

    The cheapest airlines for a one-way flight from Rochester to Chicago are Southwest ($108), American Airlines ($123), and United Airlines ($134).

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

    The top 3 most reliable airlines when flying from Rochester to Chicago are Republic Airways (91%), Japan Airlines (90%) and ANA (88%).

  • What are the cheapest flights from Rochester to Chicago?

    The cheapest flight price from Rochester to Chicago is $159. On average you can expect to pay $1,008. The most popular route, (Greater Rochester Intl - Chicago O'Hare Intl), can usually be booked for $185.

  • 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, February is the cheapest month in which you can book a flight from Rochester to Chicago (average of $75). Flying from Rochester to Chicago in June is currently the most expensive (average of $293). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 2,558,603 searches. Data last updated June 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$260Average$434FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$283Average$442FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$440FlexibilityNo cancel feeOn-time63%

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