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$86+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Apr 1 — Apr 81
Wed 4/1
Wed 4/8
1 adult, Economy
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Cheapflights Tip: The best prices from Greater Rochester Intl to Chicago are usually found in March or September, booked 68 days in advance, depart on a Wednesday or Thursday 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 March 2, 2026.

This Delta deal was found by Cheapflights users on 2/28. 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 4/185:48 pm
ROC
-
ORD
1 stop3h 52m
Delta
Mon 4/206:04 am
ORD
-
ROC
1 stop17h 39m
Delta
Deal found 2/28$319
This Southwest deal was found by Cheapflights users on 2/26. 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.
Sat 4/2512:20 pm
ROC
-
MDW
2 stops8h 45m
Southwest
Tue 4/287:50 am
MDW
-
ROC
2 stops7h 50m
Southwest
Deal found 2/26$319
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 4/811:40 am
ROC
-
ORD
2 stops25h 10m
Multiple Airlines
Wed 4/151:27 pm
ORD
-
ROC
1 stop18h 56m
Multiple Airlines
Deal found 2/27$322
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Fri 4/241:25 pm
ROC
-
ORD
Nonstop2h 12m
United Airlines
Sun 4/267:06 am
ORD
-
ROC
Nonstop1h 56m
United Airlines
Deal found 2/26$323
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Thu 5/146:30 am
ROC
-
ORD
Nonstop2h 07m
United Airlines
Mon 5/186:05 pm
ORD
-
ROC
Nonstop1h 50m
United Airlines
Deal found 2/26$325
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 4/81:12 pm
ROC
-
MDW
1 stop20h 14m
Multiple Airlines
Wed 4/156:30 am
MDW
-
ROC
2 stops25h 15m
Multiple Airlines
Deal found 2/27$325
This Southwest deal was found by Cheapflights users on 2/27. 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 4/86:40 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Wed 4/156:10 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 2/27$330
This Southwest deal was found by Cheapflights users on 2/25. 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 4/156:40 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Fri 4/1711:45 am
MDW
-
ROC
1 stop3h 50m
Southwest
Deal found 2/25$333
This Southwest deal was found by Cheapflights users on 2/28. 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 4/1812:20 pm
ROC
-
MDW
2 stops8h 45m
Southwest
Mon 4/2012:50 pm
MDW
-
ROC
2 stops9h 20m
Southwest
Deal found 2/28$334
This Delta deal was found by Cheapflights users on 2/26. 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.
Mon 3/236:16 pm
ROC
-
ORD
1 stop6h 38m
Delta
Mon 3/306:00 am
ORD
-
ROC
1 stop4h 35m
Delta
Deal found 2/26$335
This Delta deal was found by Cheapflights users on 2/26. 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.
Thu 5/141:00 pm
ROC
-
ORD
1 stop6h 05m
Delta
Mon 5/187:00 am
ORD
-
ROC
1 stop3h 59m
Delta
Deal found 2/26$337
This Delta deal was found by Cheapflights users on 2/26. 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.
Wed 4/226:13 pm
ROC
-
MDW
1 stop5h 15m
Delta
Sat 4/255:21 pm
MDW
-
ROC
1 stop5h 23m
Delta
Deal found 2/26$337

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 March 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Delta)

One-way from

$86
(Priceline)

Popular in

December

Cheapest in

March

Average price

$315

Good round-trip deal

$372 or less

Good one-way deal

$171 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. 12% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 2, 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

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 3/24

6:50 pm-7:45 pm

Nonstop1h 55m

Chicago Midway

Thu 3/26

6:35 am-11:45 am

1 stop4h 10m

$341

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 4/28

6:40 pm-7:30 pm

Nonstop1h 50m

Chicago Midway

Fri 5/1

12:50 pm-3:25 pm

Nonstop1h 35m

$343

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 3/25

10:09 am-12:29 pm

1 stop3h 20m

Chicago Midway

Thu 4/2

9:35 am-3:42 pm

1 stop5h 07m

$348

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 3/23

6:16 pm-10:31 pm

1 stop5h 15m

Chicago Midway

Mon 3/30

6:07 pm-11:59 pm

1 stop4h 52m

$357

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Fri 4/24

6:13 pm-11:59 pm

1 stop6h 46m

Chicago O'Hare Intl

Mon 4/27

11:00 am-3:25 pm

1 stop3h 25m

$363

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Wed 3/25

6:45 am-7:55 am

Nonstop2h 10m

Chicago O'Hare Intl

Mon 3/30

8:45 am-2:15 pm

1 stop4h 30m

$376

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 4/16

5:10 pm-12:05 am

1 stop7h 55m

Chicago Midway

Sun 4/19

1:15 pm-12:05 am

2 stops9h 50m

$385

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 4/8

12:35 pm-7:45 pm

2 stops8h 10m

Chicago Midway

Wed 4/15

5:00 pm-10:05 pm

1 stop4h 05m

$390

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 3/7

8:10 am-9:10 am

Nonstop2h 00m

Chicago Midway

Wed 3/18

12:45 pm-3:15 pm

Nonstop1h 30m

$392

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 4/3

6:00 am-8:53 am

1 stop3h 53m

Chicago Midway

Mon 4/6

6:34 pm-10:59 pm

1 stop3h 25m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/27

Showing 1-10 of 42 resultsSorted by cheapest first
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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 March.
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

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 February 27, 2026.

To ensure you get the cheapest price possible for a flight from Rochester to Chicago, you should look to book at least 59 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 $236). 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 March 2, 2026.

It’s typically best to fly out from Rochester to Chicago in the afternoon. Doing so could potentially save you 18% 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 February 21, 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. Sunday at noon 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 March 2, 2026.

The most flights from ROC to CHI are scheduled on a Friday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (11 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 March 2, 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
4,306 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
8.0
Very good
4,306 reviews
Southwest
8.0
Very good
4,306 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Delta
7.9
Good
8,237 reviews
Southwest
8.0
Very good
4,306 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
United Airlines
7.4
Good
9,375 reviews
Southwest
8.0
Very good
4,306 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
American Airlines
7.1
Good
11,369 reviews
Southwest
8.0
Very good
4,306 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

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 19 outbound flights to Chicago per day.

  • How long is the flight from Rochester to Chicago?

    Southwest, Delta, and United Airlines can get you from Rochester to Chicago in just under 1h 55m. Your travel time can differ by up to 1h 25m. 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 $217, 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 $249 and $303, respectively. American Airlines is priced at 42% 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 Qatar Airways (98%), Envoy Air (88%) and Japan Airlines (80%).

  • What are the cheapest flights from Rochester to Chicago?

    The cheapest flight price from Rochester to Chicago is $125. On average you can expect to pay $1,056. 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 $236). 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

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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 March 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$217Average$398FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$249Average$370FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$303Average$391FlexibilityNo cancel feeOn-time63%

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