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$93+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
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 28, 2025.

This United Airlines deal was found by Cheapflights users on 12/25. 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.
Sat 12/276:00 amROC - ORD
Nonstop2h 27mUnited Airlines
Thu 1/110:48 amORD - ROC
Nonstop2h 02mUnited Airlines
Deal found 12/25$455
This United Airlines deal was found by Cheapflights users on 12/26. 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.
Tue 12/307:45 pmROC - ORD
1 stop4h 59mUnited Airlines
Thu 1/11:24 pmORD - ROC
1 stop4h 22mUnited Airlines
Deal found 12/26$475
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:13 pmROC - ORD
1 stop5h 50mDelta
Wed 12/319:41 amORD - ROC
1 stop6h 26mDelta
Deal found 12/27$497
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:15 amROC - MDW
1 stop3h 34mDelta
Wed 12/316:00 amMDW - ROC
1 stop6h 16mDelta
Deal found 12/27$497
This Delta deal was found by Cheapflights users on 12/28. 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.
Tue 12/306:15 amROC - ORD
1 stop3h 46mDelta
Sat 1/35:30 amORD - ROC
1 stop5h 32mDelta
Deal found 12/28$509
This United Airlines deal was found by Cheapflights users on 12/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:21 pmROC - ORD
Nonstop2h 27mUnited Airlines
Wed 12/311:30 pmORD - ROC
Nonstop1h 50mUnited Airlines
Deal found 12/27$512
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:15 amROC - ORD
1 stop3h 46mDelta
Sun 1/47:00 amORD - ROC
1 stop3h 24mDelta
Deal found 12/27$531
This American Airlines deal was found by Cheapflights users on 12/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:27 pmROC - ORD
Nonstop2h 13mAmerican Airlines
Sat 1/38:59 amORD - ROC
Nonstop1h 57mAmerican Airlines
Deal found 12/28$533
This American Airlines deal was found by Cheapflights users on 12/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:21 pmROC - ORD
Nonstop2h 27mAmerican Airlines
Wed 12/313:56 pmORD - ROC
Nonstop1h 53mAmerican Airlines
Deal found 12/27$534
This United Airlines deal was found by Cheapflights users on 12/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:20 amROC - ORD
Nonstop2h 27mUnited Airlines
Sun 1/47:10 amORD - ROC
1 stop4h 46mUnited Airlines
Deal found 12/27$543
This Southwest deal was found by Cheapflights users on 12/25. 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.
Sat 12/275:25 amROC - MDW
1 stop4h 20mSouthwest
Thu 1/13:10 pmMDW - ROC
Nonstop1h 35mSouthwest
Deal found 12/25$545
This Southwest deal was found by Cheapflights users on 12/26. 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.
Tue 12/307:30 amROC - MDW
Nonstop1h 55mSouthwest
Thu 1/13:10 pmMDW - ROC
Nonstop1h 35mSouthwest
Deal found 12/26$588

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 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$228
(Kiwi.com)

One-way from

$93
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$439

Good round-trip deal

$276 or less

Good one-way deal

$165 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. 8% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 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 28, 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

Tue 1/27

6:30 am-5:43 pm

2 stops12h 13m

Chicago O'Hare Intl

Fri 1/30

7:45 am-11:28 pm

2 stops14h 43m

$234

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 2/26

10:13 am-11:05 pm

1 stop13h 52m

Chicago O'Hare Intl

Sun 3/1

3:40 pm-5:40 pm

2 stops25h 00m

$247

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Fri 1/30

6:30 am-5:43 pm

2 stops12h 13m

Chicago O'Hare Intl

Mon 2/2

7:44 am-2:40 pm

1 stop5h 56m

$252

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Sat 1/24

6:30 am-5:43 pm

2 stops12h 13m

Chicago O'Hare Intl

Mon 1/26

7:45 am-11:28 pm

2 stops14h 43m

$282

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Fri 2/6

6:00 am-12:05 pm

1 stop7h 05m

Chicago O'Hare Intl

Fri 2/6

2:40 pm-2:13 pm

2 stops22h 33m

$314

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 1/15

7:41 pm-9:43 am

1 stop15h 02m

Chicago O'Hare Intl

Sun 1/18

7:00 am-7:01 pm

1 stop11h 01m

$323

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 4/23

10:13 am-7:48 pm

1 stop10h 35m

Chicago O'Hare Intl

Mon 4/27

5:30 am-5:40 pm

2 stops11h 10m

$326

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 1/8

7:41 pm-10:04 pm

1 stop27h 23m

Chicago O'Hare Intl

Sun 1/11

7:00 am-7:01 pm

1 stop11h 01m

$333

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 2/21

3:15 pm-4:20 pm

Nonstop2h 05m

Chicago Midway

Mon 2/23

6:10 pm-8:45 pm

Nonstop1h 35m

$336

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 2/26

6:20 am-7:30 am

Nonstop2h 10m

Chicago O'Hare Intl

Mon 3/2

10:38 am-1:43 pm

Nonstop2h 05m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 35 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 26, 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 28, 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 20, 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.

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 December 28, 2025.

The most flights from ROC to CHI are scheduled on a Friday (25 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (18 on average).

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 28, 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
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
8,019 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
9,113 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
11,073 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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 21 outbound flights to Chicago per day.

  • How long is the flight from Rochester to Chicago?

    JetBlue, United Airlines, and Southwest can get you from Rochester to Chicago in just under 2h 05m. Your travel time can differ by up to 10h 08m. 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 44% 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 $118. On average you can expect to pay $915. The most popular route, (Greater Rochester Intl - Chicago O'Hare Intl), can usually be booked for $228.

  • 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$197Average$382FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$240Average$354FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$303Average$393FlexibilityNo cancel feeOn-time63%

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