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$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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Greater Rochester Intl to Chicago are usually found in March or January, 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 December 18, 2025.

This Delta deal was found by Cheapflights users on 12/15. 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 12/256:15 amROC - MDW
1 stop3h 34mDelta
Tue 1/66:45 amMDW - ROC
1 stop5h 28mDelta
Deal found 12/15$397
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/202:25 pmROC - ORD
2 stops20h 24mUnited Airlines
Sun 12/211:30 pmORD - ROC
Nonstop1h 50mUnited Airlines
Deal found 12/16$424
This Delta deal was found by Cheapflights users on 12/15. 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 12/256:15 amROC - MDW
1 stop3h 34mDelta
Mon 1/56:45 amMDW - ROC
1 stop5h 31mDelta
Deal found 12/15$437
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/316:20 amROC - ORD
Nonstop2h 27mUnited Airlines
Sat 1/36:19 pmORD - ROC
Nonstop1h 56mUnited Airlines
Deal found 12/16$445
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/246:20 amROC - ORD
Nonstop2h 27mUnited Airlines
Sat 12/2710:48 amORD - ROC
Nonstop2h 02mUnited Airlines
Deal found 12/17$455
This Delta deal was found by Cheapflights users on 12/15. 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 12/296:15 amROC - MDW
1 stop3h 34mDelta
Tue 1/66:14 pmMDW - ROC
1 stop3h 38mDelta
Deal found 12/15$455
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/246:00 amROC - ORD
1 stop5h 03mAmerican Airlines
Sat 12/278:58 pmORD - ROC
Nonstop2h 01mAmerican Airlines
Deal found 12/17$465
This Delta deal was found by Cheapflights users on 12/15. 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 12/2412:04 pmROC - MDW
1 stop6h 22mDelta
Mon 12/296:08 pmMDW - ROC
1 stop3h 58mDelta
Deal found 12/15$465
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/305:15 amROC - ORD
Nonstop2h 18mAmerican Airlines
Sun 1/48:46 pmORD - ROC
Nonstop2h 03mAmerican Airlines
Deal found 12/16$469
This Delta deal was found by Cheapflights users on 12/15. 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 12/256:15 amROC - MDW
1 stop3h 34mDelta
Mon 1/196:35 pmMDW - ROC
1 stop3h 17mDelta
Deal found 12/15$470
This Delta deal was found by Cheapflights users on 12/17. 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 12/206:15 amROC - ORD
1 stop3h 46mDelta
Thu 12/256:02 pmORD - ROC
1 stop4h 04mDelta
Deal found 12/17$475
This Delta deal was found by Cheapflights users on 12/15. 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 12/206:15 amROC - MDW
1 stop3h 34mDelta
Wed 12/246:08 pmMDW - ROC
1 stop3h 58mDelta
Deal found 12/15$475

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$187
(Mytrip)

One-way from

$76
(JetBlue)

Popular in

November

Cheapest in

March

Average price

$384

Good round-trip deal

$284 or less

Good one-way deal

$175 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. 9% potential increase in price ($36 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 December 2025
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 December 18, 2025.
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 - ORD

ROCORD

Greater Rochester Intl

Sat 1/24

2:48 pm-8:03 am

2 stops18h 15m

Chicago O'Hare Intl

Sun 1/25

10:35 am-1:39 pm

Nonstop2h 04m

$233

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Sun 2/1

11:31 am-11:22 am

2 stops24h 51m

Chicago O'Hare Intl

Fri 2/6

5:15 am-5:00 pm

2 stops10h 45m

$312

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Wed 1/7

1:26 pm-2:55 pm

Nonstop2h 29m

Chicago O'Hare Intl

Wed 1/14

1:55 pm-4:48 pm

Nonstop1h 53m

$313

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 2/5

6:00 am-7:24 am

Nonstop2h 24m

Chicago O'Hare Intl

Mon 2/9

9:11 pm-11:58 pm

Nonstop1h 47m

$333

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Wed 1/7

6:00 am-10:55 am

1 stop5h 55m

Chicago O'Hare Intl

Wed 1/7

5:20 pm-11:13 pm

1 stop4h 53m

$333

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 1/8

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

Mon 1/12

2:20 pm-4:55 pm

Nonstop1h 35m

$333

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Mon 1/19

6:00 am-7:24 am

Nonstop2h 24m

Chicago O'Hare Intl

Mon 1/19

9:11 pm-11:58 pm

Nonstop1h 47m

$333

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 2/2

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

Thu 2/5

6:10 pm-8:45 pm

Nonstop1h 35m

$333

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Mon 1/12

1:26 pm-2:55 pm

Nonstop2h 29m

Chicago O'Hare Intl

Tue 1/13

8:52 am-2:13 pm

1 stop4h 21m

$333

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Mon 1/26

5:23 pm-6:49 pm

Nonstop2h 26m

Chicago O'Hare Intl

Thu 1/29

6:08 pm-9:04 pm

Nonstop1h 56m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 40 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Rochester-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 12, 2025.

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 January is currently the most expensive (average of $219). 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 December 18, 2025.

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 December 13, 2025.

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.

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 December 18, 2025.
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
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

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
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

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
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

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
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

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 10 outbound flights to Chicago per day.

  • How long is the flight from Rochester to Chicago?

    United Airlines and Southwest can get you from Rochester to Chicago in just under 2h 15m. Your travel time can differ by up to 16h. 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 $239 and $303, respectively. American Airlines is priced at 43% 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 American Airlines ($118), United Airlines ($124), and Delta ($144).

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

    The top 3 most reliable airlines when flying from Rochester to Chicago are SkyWest Airlines (100%), Qatar Airways (80%) and Emirates (75%).

  • What are the cheapest flights from Rochester to Chicago?

    The cheapest flight price from Rochester to Chicago is $120. On average you can expect to pay $1,025. The most popular route, (Greater Rochester Intl - Chicago O'Hare Intl), can usually be booked for $187.

  • 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 January is currently the most expensive (average of $219). 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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Alternative routes for Rochester to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$199Average$372FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$236Average$351FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$303Average$393FlexibilityNo cancel feeOn-time63%

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