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$77+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheapflights Tip: The best prices from Greater Rochester Intl to Chicago are usually found in January or March, booked 76 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

Cheap 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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$268
(Kiwi.com)

One-way from

$77
(JetBlue)

Popular in

October

Cheapest in

January

Average price

$364

Good round-trip deal

$334 or less

Good one-way deal

$156 or less
Provider with most accurate pricing for Greater Rochester Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Greater Rochester Intl-Chicago (CHI) flights.
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From Greater Rochester Intl to Chicago (CHI)
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One-way flight from Greater Rochester Intl to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Greater Rochester Intl to Chicago (CHI).
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Price to beat on a one-way flight from Greater Rochester Intl to Chicago (CHI).
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Find 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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 12/76:56 pmROC - ORD
1 stop19h 20mMultiple Airlines
Wed 12/1012:09 pmORD - ROC
1 stop28h 42mMultiple Airlines
Deal found 11/6$268
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 12/76:56 pmROC - ORD
2 stops22h 58mMultiple Airlines
Sun 12/147:20 amORD - ROC
1 stop9h 31mMultiple Airlines
Deal found 11/6$269
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/46:56 pmROC - ORD
1 stop19h 20mMultiple Airlines
Mon 12/87:20 amORD - ROC
1 stop9h 31mMultiple Airlines
Deal found 11/6$270
This JetBlue deal was found by Cheapflights users on 11/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:05 pmROC - ORD
1 stop6h 47mJetBlue
Tue 12/167:00 amORD - ROC
1 stop7h 10mJetBlue
Deal found 11/6$271
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/176:57 pmROC - ORD
1 stop5h 31mMultiple Airlines
Thu 11/2012:55 pmORD - ROC
1 stop21h 43mMultiple Airlines
Deal found 11/4$272
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/136:10 amROC - ORD
1 stop4h 26mUnited Airlines
Tue 12/1610:40 amORD - ROC
Nonstop1h 51mUnited Airlines
Deal found 11/5$273
This Southwest deal was found by Cheapflights users on 11/4. 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 12/125:35 pmROC - MDW
1 stop6h 25mSouthwest
Tue 12/163:15 pmMDW - ROC
Nonstop1h 35mSouthwest
Deal found 11/4$273
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/311:40 amROC - ORD
1 stop7h 35mMultiple Airlines
Mon 12/87:20 amORD - ROC
1 stop9h 31mMultiple Airlines
Deal found 11/6$274
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/1011:40 amROC - ORD
2 stops13h 29mMultiple Airlines
Sun 12/147:20 amORD - ROC
1 stop9h 31mMultiple Airlines
Deal found 11/6$275
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/246:57 pmROC - ORD
2 stops29h 09mMultiple Airlines
Tue 12/212:32 pmORD - ROC
1 stop21h 28mMultiple Airlines
Deal found 11/4$277
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/202:20 pmROC - ORD
2 stops19h 41mMultiple Airlines
Tue 12/212:32 pmORD - ROC
1 stop21h 28mMultiple Airlines
Deal found 11/4$278
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sun 11/165:03 pmROC - ORD
2 stops25h 15mMultiple Airlines
Fri 11/2112:17 pmORD - ROC
1 stop5h 00mMultiple Airlines
Deal found 11/4$279

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 November 6, 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 2/17

1:35 pm-2:47 pm

Nonstop2h 12m

Chicago O'Hare Intl

Tue 2/24

8:50 am-2:14 pm

1 stop4h 24m

$273

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 12/12

3:25 pm-4:20 pm

Nonstop1h 55m

Chicago Midway

Tue 12/16

2:10 pm-10:30 pm

2 stops7h 20m

$278

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 2/17

6:13 pm-11:57 pm

1 stop6h 44m

Chicago O'Hare Intl

Tue 2/24

9:35 am-5:52 pm

1 stop7h 17m

$283

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Sun 2/1

6:15 pm-11:57 pm

1 stop6h 42m

Chicago O'Hare Intl

Thu 2/5

10:45 am-5:53 pm

1 stop6h 08m

$283

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 3/3

6:00 am-10:33 am

1 stop5h 33m

Chicago O'Hare Intl

Wed 3/4

6:30 am-12:06 pm

1 stop4h 36m

$283

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 2/17

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Tue 2/24

9:34 am-3:23 pm

1 stop4h 49m

$283

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 3/3

12:59 pm-5:45 pm

1 stop5h 46m

Chicago Midway

Wed 3/4

6:17 pm-10:54 pm

1 stop3h 37m

$283

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 2/1

6:15 pm-10:26 pm

1 stop5h 11m

Chicago Midway

Thu 2/5

9:34 am-3:28 pm

1 stop4h 54m

$283

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Mon 12/15

5:30 pm-6:48 pm

Nonstop2h 18m

Chicago O'Hare Intl

Tue 12/16

5:50 pm-8:34 pm

Nonstop1h 44m

$292

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 12/3

6:30 pm-7:25 pm

Nonstop1h 55m

Chicago Midway

Mon 12/8

3:15 pm-5:50 pm

Nonstop1h 35m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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 November.
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 October 31, 2025.

To ensure you get the cheapest price possible for a flight from Rochester to Chicago, you should look to book at least 76 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 November 6, 2025.

It’s typically best to fly out from Rochester to Chicago in the afternoon. Doing so could potentially save you 20% 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 November 6, 2025.

The most flights from ROC to CHI are scheduled on a Wednesday (28 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 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 November 6, 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
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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?

    United Airlines, Southwest, and Delta can get you from Rochester to Chicago in just under 1h 55m. Your travel time can differ by up to 4h 49m. 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 $198, 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 41% 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 JetBlue ($77), United Airlines ($132), and Delta ($134).

  • 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 (98%), ANA (88%) and Republic Airways (84%).

  • 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 $1,078. The most popular route, (Greater Rochester Intl - Chicago O'Hare Intl), can usually be booked for $222.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$365FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$240Average$346FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$303Average$393FlexibilityNo cancel feeOn-time63%

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