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$222+ Cheap flights from Rochester, MN (RST) 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
RST — CHI
Jul 30 — Aug 61
Thu 7/30
Thu 8/6
1 adult, Economy
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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 June 30, 2026.

This Delta deal was found by Cheapflights users on 6/26. 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.
Fri 9/114:45 pm
RST
-
ORD
1 stop4h 48m
Delta
Mon 9/216:00 am
ORD
-
RST
1 stop4h 56m
Delta
Deal found 6/26$248
This Delta deal was found by Cheapflights users on 6/26. 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.
Tue 9/85:15 am
RST
-
MDW
1 stop3h 33m
Delta
Fri 9/187:13 pm
MDW
-
RST
1 stop3h 25m
Delta
Deal found 6/26$248
This Delta deal was found by Cheapflights users on 6/26. 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.
Wed 9/911:36 am
RST
-
ORD
1 stop5h 57m
Delta
Wed 9/168:55 am
ORD
-
RST
2 stops7h 10m
Delta
Deal found 6/26$254
This Delta deal was found by Cheapflights users on 6/26. 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.
Tue 9/85:15 am
RST
-
MDW
1 stop3h 33m
Delta
Wed 9/169:29 am
MDW
-
RST
2 stops6h 36m
Delta
Deal found 6/26$254
This United Airlines deal was found by Cheapflights users on 6/25. 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 10/2810:47 am
RST
-
ORD
Nonstop1h 37m
United Airlines
Sun 11/18:40 am
ORD
-
RST
Nonstop1h 26m
United Airlines
Deal found 6/25$256
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:15 am
RST
-
ORD
2 stops7h 44m
Delta
Wed 10/212:00 pm
ORD
-
RST
2 stops8h 44m
Delta
Deal found 6/29$259
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:23 am
RST
-
MDW
2 stops6h 42m
Delta
Sat 10/319:29 am
MDW
-
RST
2 stops6h 13m
Delta
Deal found 6/29$259
This Delta deal was found by Cheapflights users on 6/26. 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.
Fri 9/184:45 pm
RST
-
ORD
1 stop4h 48m
Delta
Mon 9/216:00 am
ORD
-
RST
1 stop4h 56m
Delta
Deal found 6/26$263
This Delta deal was found by Cheapflights users on 6/28. 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.
Fri 8/711:33 am
RST
-
MDW
1 stop6h 28m
Delta
Sat 8/87:25 pm
MDW
-
RST
1 stop3h 02m
Delta
Deal found 6/28$263
This Delta deal was found by Cheapflights users on 6/28. 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.
Fri 10/25:15 am
RST
-
MDW
2 stops7h 24m
Delta
Sun 10/49:59 am
MDW
-
RST
1 stop6h 06m
Delta
Deal found 6/28$269
This Delta deal was found by Cheapflights users on 6/26. 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.
Sat 9/195:15 am
RST
-
ORD
1 stop3h 23m
Delta
Sat 9/196:24 pm
ORD
-
RST
1 stop16h 32m
Delta
Deal found 6/26$271
This Delta deal was found by Cheapflights users on 6/26. 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.
Mon 9/144:45 pm
RST
-
MDW
1 stop20h 35m
Delta
Mon 9/217:13 pm
MDW
-
RST
1 stop3h 25m
Delta
Deal found 6/26$271

Find flight deals from Rochester to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Rochester (RST) 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 June 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$248
(Delta)

One-way from

$222
(Delta)

Popular in

October

Cheapest in

November

Average price

$418

Good round-trip deal

$407 or less

Good one-way deal

$388 or less
Provider with most accurate pricing for Rochester-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Rochester-Chicago (CHI) flights.
Search Deals
From Rochester to Chicago (CHI)
Search Deals
One-way flight from Rochester to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Rochester to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Rochester 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 June 30, 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

RST - ORD

RSTORD

Rochester

Wed 10/28

11:15 am-2:57 pm

1 stop3h 42m

Chicago O'Hare Intl

Sun 11/1

7:40 pm-10:46 pm

1 stop3h 06m

$248

RochesterChicago

RST - ORD

RSTORD

Rochester

Fri 9/18

4:45 pm-9:33 pm

1 stop4h 48m

Chicago O'Hare Intl

Mon 9/21

5:50 pm-10:38 pm

1 stop4h 48m

$248

RochesterChicago

RST - ORD

RSTORD

Rochester

Fri 9/11

4:45 pm-9:33 pm

1 stop4h 48m

Chicago O'Hare Intl

Mon 9/14

6:00 am-10:56 am

1 stop4h 56m

$248

RochesterChicago

RST - ORD

RSTORD

Rochester

Fri 9/11

5:15 am-8:30 am

1 stop3h 15m

Chicago O'Hare Intl

Sun 9/13

6:00 am-10:56 am

1 stop4h 56m

$248

RochesterChicago

RST - ORD

RSTORD

Rochester

Fri 10/2

11:36 am-8:30 pm

2 stops8h 54m

Chicago O'Hare Intl

Sun 10/4

6:00 am-10:56 am

1 stop4h 56m

$254

RochesterChicago

RST - ORD

RSTORD

Rochester

Wed 9/23

4:45 pm-9:33 pm

1 stop4h 48m

Chicago O'Hare Intl

Wed 10/21

2:00 pm-10:44 pm

2 stops8h 44m

$254

RochesterChicago

RST - ORD

RSTORD

Rochester

Sat 9/5

5:28 am-1:50 pm

2 stops8h 22m

Chicago O'Hare Intl

Wed 9/9

1:55 pm-10:38 pm

2 stops8h 43m

$259

RochesterChicago

RST - MDW

RSTMDW

Rochester

Fri 8/7

11:33 am-6:01 pm

1 stop6h 28m

Chicago Midway

Sat 8/8

7:25 pm-10:27 pm

1 stop3h 02m

$263

RochesterChicago

RST - MDW

RSTMDW

Rochester

Fri 10/2

5:15 am-8:48 am

1 stop3h 33m

Chicago Midway

Sun 10/4

9:59 am-4:05 pm

1 stop6h 06m

$263

RochesterChicago

RST - MDW

RSTMDW

Rochester

Thu 9/3

5:28 am-8:39 am

1 stop3h 11m

Chicago Midway

Wed 9/9

9:29 am-4:05 pm

2 stops6h 36m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 32 resultsSorted by cheapest first
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3
4

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 June.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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, Minnesota-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Rochester, Minnesota-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Rochester, Minnesota-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Rochester, Minnesota-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, Minnesota-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

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

Currently, May is the cheapest month in which you can book a flight from Rochester, Minnesota to Chicago (average of $168). Flying from Rochester, Minnesota to Chicago in February is currently the most expensive (average of $348). 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 RST 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 June 30, 2026.

A simple way to save on the total cost of your ticket is to fly from Rochester, Minnesota to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 23% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip from Rochester, Minnesota to Chicago?

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

Use this chart to determine the cheapest time to fly round-trip from Rochester to Chicago. Price data was last updated on June 27, 2026.

Travelers seeking maximum savings on their Rochester, Minnesota to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Wednesday 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 June 30, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Rochester to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,901 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
9,901 reviews
United Airlines
7.4
Good
9,901 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.1
Good
11,762 reviews
United Airlines
7.4
Good
9,901 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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?

    For a flight from Rochester to Chicago, you will be flying from Rochester. Rochester (RST) is just 7.0 mi from the center of the city. Rochester is the only Rochester airport and it handles 3 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Rochester on a regular basis.

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

    Delta can get you from Rochester, Minnesota to Chicago in just under 3h 42m. Your travel time can differ by up to . There are 268 mi between Rochester, Minnesota and Chicago.

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

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at $168. Another option worth looking into is American Airlines, starting at $329 round trip. United Airlines is priced at 61% lower than the current average price of a flight leaving 3 months from now.

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

    The top 3 most reliable airlines when flying from Rochester, Minnesota to Chicago are Envoy Air (85%), Qatar Airways (83%) and American Airlines (76%).

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

    Looking for the cheapest flight from Rochester, Minnesota to Chicago? While on average our users pay $506, our data indicates the cheapest price to be $258. The most popular route (Rochester - Chicago O'Hare Intl), is priced around $248.

  • 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, Minnesota to Chicago?

    Currently, May is the cheapest month in which you can book a flight from Rochester, Minnesota to Chicago (average of $168). Flying from Rochester, Minnesota to Chicago in February is currently the most expensive (average of $348). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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Top 2 airlines flying from Rochester to Chicago

Discover the top 2 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 June 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$168Average$263FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$329Average$448FlexibilityNo cancel feeOn-time71%

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