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$103+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheapflights Tip: The best prices from Greater Rochester Intl to Chicago are usually found in September or October, booked 88 days in advance, depart on a Wednesday or Tuesday 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 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Mon 4/66:20 pm
ROC
-
ORD
2 stops17h 24m
Multiple Airlines
Wed 4/297:15 pm
ORD
-
ROC
1 stop13h 08m
Multiple Airlines
Deal found 3/24$326
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Wed 4/811:40 am
ROC
-
ORD
1 stop25h 44m
Multiple Airlines
Sat 5/27:15 pm
ORD
-
ROC
1 stop13h 08m
Multiple Airlines
Deal found 3/24$327
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Thu 4/169:25 am
ROC
-
ORD
2 stops14h 14m
Multiple Airlines
Sun 4/191:12 pm
ORD
-
ROC
1 stop27h 28m
Multiple Airlines
Deal found 3/25$328
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Fri 4/106:20 pm
ROC
-
ORD
2 stops17h 48m
Multiple Airlines
Sat 4/251:27 pm
ORD
-
ROC
1 stop18h 56m
Multiple Airlines
Deal found 3/25$329
This Delta deal was found by Cheapflights users on 3/25. 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 4/145:48 pm
ROC
-
ORD
1 stop3h 52m
Delta
Thu 4/1610:45 am
ORD
-
ROC
1 stop5h 23m
Delta
Deal found 3/25$330
This Delta deal was found by Cheapflights users on 3/25. 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 4/146:13 pm
ROC
-
MDW
1 stop5h 15m
Delta
Thu 4/169:27 am
MDW
-
ROC
1 stop4h 55m
Delta
Deal found 3/25$330
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/910:13 am
ROC
-
ORD
1 stop13h 37m
Multiple Airlines
Tue 4/288:52 pm
ORD
-
ROC
1 stop13h 08m
Multiple Airlines
Deal found 3/24$331
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Thu 4/910:13 am
ROC
-
ORD
1 stop10h 38m
Multiple Airlines
Sat 4/181:27 pm
ORD
-
ROC
1 stop18h 56m
Multiple Airlines
Deal found 3/25$332
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Thu 4/910:13 am
ROC
-
ORD
1 stop8h 02m
Multiple Airlines
Thu 4/304:28 pm
ORD
-
ROC
2 stops24h 12m
Multiple Airlines
Deal found 3/27$333
This United Airlines deal was found by Cheapflights users on 3/25. 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 5/206:30 am
ROC
-
ORD
Nonstop2h 07m
United Airlines
Mon 5/256:30 pm
ORD
-
ROC
Nonstop1h 53m
United Airlines
Deal found 3/25$334
This Southwest deal was found by Cheapflights users on 3/24. 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.
Tue 4/216:40 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Tue 4/2812:45 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 3/24$334
This Delta deal was found by Cheapflights users on 3/26. 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 4/166:15 am
ROC
-
ORD
1 stop5h 04m
Delta
Mon 4/205:15 am
ORD
-
ROC
1 stop5h 38m
Delta
Deal found 3/26$335

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 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$326
(American Airlines)

One-way from

$103
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$366

Good round-trip deal

$360 or less

Good one-way deal

$189 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. 7% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 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 28, 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 - MDW

ROCMDW

Greater Rochester Intl

Wed 6/10

6:21 pm-10:17 pm

1 stop4h 56m

Chicago Midway

Fri 6/12

5:11 pm-11:57 pm

1 stop5h 46m

$354

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 5/28

7:50 pm-8:40 pm

Nonstop1h 50m

Chicago Midway

Sat 5/30

5:25 pm-11:10 pm

1 stop4h 45m

$374

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 4/16

6:00 am-9:38 am

1 stop4h 38m

Chicago O'Hare Intl

Sun 4/19

6:20 pm-9:09 pm

Nonstop1h 49m

$384

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Fri 4/24

6:20 am-7:26 am

Nonstop2h 06m

Chicago O'Hare Intl

Sun 4/26

6:20 pm-9:09 pm

Nonstop1h 49m

$392
Quickest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 6/5

7:35 pm-8:25 pm

Nonstop1h 50m

Chicago Midway

Sun 6/7

7:50 pm-10:25 pm

Nonstop1h 35m

$392

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 4/14

5:35 pm-6:45 pm

Nonstop2h 10m

Chicago O'Hare Intl

Thu 4/16

6:20 pm-9:09 pm

Nonstop1h 49m

$402

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 4/24

5:10 pm-12:05 am

1 stop7h 55m

Chicago Midway

Mon 4/27

6:45 pm-9:20 pm

Nonstop1h 35m

$402

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Fri 4/17

10:44 am-11:56 am

Nonstop2h 12m

Chicago O'Hare Intl

Sun 4/19

7:06 am-10:02 am

Nonstop1h 56m

$403

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 5/23

8:05 am-8:55 am

Nonstop1h 50m

Chicago Midway

Tue 5/26

6:10 pm-8:45 pm

Nonstop1h 35m

$403

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Fri 6/5

6:15 am-7:23 am

Nonstop2h 08m

Chicago O'Hare Intl

Sun 6/7

12:08 pm-3:05 pm

Nonstop1h 57m

$411

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 43 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 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, New York-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Rochester, New York-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Rochester, New York-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Rochester, New York-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, New York-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, New York 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 March 13, 2026.

The price you pay for your flight from Rochester, New York to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, July is the cheapest month in which you can book a flight from Rochester, New York to Chicago (average of $77). Flying from Rochester, New York to Chicago in March is currently the most expensive (average of $251). 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 28, 2026.

It’s typically best to fly out from Rochester, New York to Chicago in the afternoon. Doing so could potentially save you 14% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Rochester, New York to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Rochester to Chicago. Price data was last updated on March 23, 2026.

Travelers seeking maximum savings on their Rochester, New York 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, New York 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 28, 2026.

The most flights from ROC to CHI are scheduled on a Saturday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Rochester, New York 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 28, 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
8.0
Very good
4,333 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,499 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,520 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 7 outbound flights to Chicago per day.

  • How long is the flight from Rochester, New York to Chicago?

    Airlines like Delta, Southwest, and United Airlines fly from Rochester, New York to Chicago in about 1h 50m. The time it takes to get you to your destination can typically vary by up to 3h 06m. Rochester, New York and Chicago are separated by a distance of 521 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Our cheapest airline available from Rochester, New York to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $232 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $256 and $305 round-trip. You may be able to fly from Rochester, New York to Chicago for 40% less than the average price by searching for these airlines.

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

    The top 3 most reliable airlines when flying from Rochester, New York to Chicago are Republic Airways (89%), Japan Airlines (87%) and Qatar Airways (84%).

  • What are the cheapest flights from Rochester, New York to Chicago?

    The cheapest flight price from Rochester, New York to Chicago is $124. On average you can expect to pay $1,077. The most popular route, (Greater Rochester Intl - Chicago O'Hare Intl), can usually be booked for $233.

  • 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, New York to Chicago?

    Currently, July is the cheapest month in which you can book a flight from Rochester, New York to Chicago (average of $77). Flying from Rochester, New York to Chicago in March is currently the most expensive (average of $251). 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 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$232Average$416FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$256Average$390FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$305Average$391FlexibilityNo cancel feeOn-time63%

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