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$73+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$266
(Trip.com)

One-way from

$73
(Priceline)

Popular in

October

Cheapest in

January

Average price

$431

Good round-trip deal

$298 or less

Good one-way deal

$162 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)
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. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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).
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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 October 30, 2025.

This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:24 amROC - ORD
2 stops13h 24mMultiple Airlines
Sat 12/63:26 pmORD - ROC
2 stops21h 52mMultiple Airlines
Deal found 10/29$271
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:33 pmROC - MDW
1 stop11h 56mMultiple Airlines
Sun 11/235:30 pmMDW - ROC
1 stop17h 08mMultiple Airlines
Deal found 10/28$272
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:56 pmROC - ORD
2 stops17h 12mMultiple Airlines
Sat 12/64:49 pmORD - ROC
3 stops20h 29mMultiple Airlines
Deal found 10/29$276
This Kiwi.com deal was found by Cheapflights users on 10/29. 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
Fri 11/2112:17 pmORD - ROC
1 stop5h 00mMultiple Airlines
Deal found 10/29$277
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:56 pmROC - ORD
2 stops21h 51mSpirit Airlines
Mon 12/87:10 amORD - ROC
2 stops9h 41mSpirit Airlines
Deal found 10/29$279
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:56 pmROC - ORD
2 stops17h 12mSpirit Airlines
Sun 12/147:20 amORD - ROC
1 stop9h 31mSpirit Airlines
Deal found 10/29$280
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/186:00 pmROC - MDW
1 stop28h 58mMultiple Airlines
Mon 1/56:12 amMDW - ROC
2 stops11h 05mMultiple Airlines
Deal found 10/29$282
This JetBlue deal was found by Cheapflights users on 10/29. 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.
Fri 11/215:04 pmROC - ORD
1 stop6h 32mJetBlue
Sun 11/236:00 amORD - ROC
1 stop6h 12mJetBlue
Deal found 10/29$285
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sat 12/611:40 amROC - ORD
2 stops13h 29mMultiple Airlines
Sun 12/77:20 amORD - ROC
1 stop9h 31mMultiple Airlines
Deal found 10/29$286
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/2412:33 pmROC - ORD
1 stop11h 33mMultiple Airlines
Mon 12/16:35 pmORD - ROC
2 stops39h 25mMultiple Airlines
Deal found 10/30$291
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:56 pmROC - ORD
3 stops28h 15mSpirit Airlines
Wed 12/101:34 pmORD - ROC
3 stops27h 17mSpirit Airlines
Deal found 10/29$292
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:33 pmROC - ORD
1 stop11h 33mMultiple Airlines
Sun 11/2310:12 amORD - ROC
2 stops21h 27mMultiple Airlines
Deal found 10/30$294

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 October 30, 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

Thu 12/4

9:24 am-9:48 pm

2 stops13h 24m

Chicago O'Hare Intl

Sat 12/6

12:09 pm-2:18 pm

3 stops25h 09m

$299

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 12/4

6:30 pm-7:25 pm

Nonstop1h 55m

Chicago Midway

Mon 12/8

3:15 pm-5:50 pm

Nonstop1h 35m

$311

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Sat 12/6

4:05 pm-9:52 pm

1 stop6h 47m

Chicago O'Hare Intl

Sun 12/7

7:00 am-3:10 pm

1 stop7h 10m

$312

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Mon 12/15

6:56 pm-11:08 am

2 stops17h 12m

Chicago O'Hare Intl

Fri 12/19

5:18 pm-9:30 am

1 stop15h 12m

$320

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 12/18

3:25 pm-4:20 pm

Nonstop1h 55m

Chicago Midway

Mon 1/5

5:15 pm-11:45 pm

1 stop5h 30m

$321

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 1/11

1:13 pm-9:13 am

1 stop21h 00m

Chicago Midway

Fri 1/16

3:19 pm-3:52 pm

2 stops23h 33m

$328

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Tue 12/23

7:45 pm-11:44 pm

1 stop4h 59m

Chicago O'Hare Intl

Thu 1/1

6:21 pm-11:41 pm

1 stop4h 20m

$331

RochesterChicago

ROC - ORD

ROCORD

Greater Rochester Intl

Thu 12/4

1:37 pm-2:55 pm

Nonstop2h 18m

Chicago O'Hare Intl

Sat 12/6

6:10 pm-9:00 pm

Nonstop1h 50m

$332

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 12/5

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Tue 12/9

1:14 pm-10:59 pm

1 stop8h 45m

$339

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 12/5

12:27 pm-4:18 pm

1 stop4h 51m

Chicago Midway

Mon 12/8

9:34 am-10:59 pm

1 stop12h 25m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 44 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 October.
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 24, 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 October 30, 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.

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 October 30, 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
4,243 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

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
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

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 9 outbound flights to Chicago per day.

  • How long is the flight from Rochester to Chicago?

    Southwest, JetBlue, and United Airlines can get you from Rochester to Chicago in just under 1h 55m. Your travel time can differ by up to 4h 52m. 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 $200, 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 40% 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 SkyWest Airlines (98%), ANA (87%) and Japan Airlines (85%).

  • 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 $800. The most popular route, (Greater Rochester Intl - Chicago O'Hare Intl), can usually be booked for $155.

  • 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
Merrillville
Lansing
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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$200Average$368FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$345FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$303Average$393FlexibilityNo cancel feeOn-time63%

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