Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Rochester to Chicago from $139

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Rochester to Chicago departing on 10/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Rochester to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:55 am - 12:25 pm
ROC
-
MDW
7h 30m
2 stops
Southwest Logo
6:45 am - 4:20 pm
MDW
-
ROC
8h 35m
2 stops
$307Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
6:05 am - 11:50 am
ROC
-
MDW
6h 45m
2 stops
Southwest Logo
7:40 am - 5:30 pm
MDW
-
ROC
8h 50m
2 stops
$307Southwest
Tue, Sep 1 - Tue, Sep 8
Southwest Logo
6:05 am - 1:05 pm
ROC
-
MDW
8h 00m
2 stops
Southwest Logo
8:40 am - 5:30 pm
MDW
-
ROC
7h 50m
2 stops
$307Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
3:20 pm - 10:20 pm
ROC
-
MDW
8h 00m
2 stops
Southwest Logo
7:40 am - 5:30 pm
MDW
-
ROC
8h 50m
2 stops
$307Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
11:55 am - 7:15 pm
ROC
-
MDW
8h 20m
2 stops
Southwest Logo
12:50 pm - 9:20 pm
MDW
-
ROC
7h 30m
2 stops
$307Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
11:10 am - 5:10 pm
ROC
-
MDW
7h 00m
2 stops
Southwest Logo
6:05 am - 3:25 pm
MDW
-
ROC
8h 20m
1 stop
$308Southwest
Sat, Dec 12 - Mon, Dec 14
Southwest Logo
12:30 pm - 8:10 pm
ROC
-
MDW
8h 40m
2 stops
Southwest Logo
4:00 pm - 11:40 pm
MDW
-
ROC
6h 40m
2 stops
$312Southwest
Fri, Oct 30 - Mon, Nov 2
Southwest Logo
6:45 pm - 7:35 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
5:55 am - 12:20 pm
MDW
-
ROC
5h 25m
1 stop
$315Southwest
Thu, Sep 17 - Sat, Sep 26
Delta Logo
12:32 pm - 4:57 pm
ROC
-
MDW
5h 25m
1 stop
Delta Logo
5:37 pm - 10:54 pm
MDW
-
ROC
4h 17m
1 stop
$325Delta
Wed, Sep 9 - Sat, Sep 12
Delta Logo
6:00 am - 9:17 am
ROC
-
MDW
4h 17m
1 stop
Delta Logo
6:44 pm - 10:55 pm
MDW
-
ROC
3h 11m
1 stop
$325Delta
Wed, Oct 21 - Sat, Oct 24

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Rochester to Chicago Midway Airport

Our best Delta deals on Rochester to Chicago Midway Airport flight tickets
Delta
Aug 27
ROC6:03 amGreater Rochester Intl
4h 56m
1 stop
MDW9:59 amChicago Midway
Sep 3
MDW6:42 pmChicago Midway
3h 10m
1 stop
ROC10:52 pmGreater Rochester Intl
$325
Delta
Aug 27
ROC6:03 amGreater Rochester Intl
6h 48m
1 stop
MDW11:51 amChicago Midway
Aug 29
MDW6:42 pmChicago Midway
3h 10m
1 stop
ROC10:52 pmGreater Rochester Intl
$328
Delta
Aug 21
ROC6:03 amGreater Rochester Intl
6h 48m
1 stop
MDW11:51 amChicago Midway
Aug 24
MDW6:42 pmChicago Midway
3h 10m
1 stop
ROC10:52 pmGreater Rochester Intl
$340

Southwest flights from Rochester to Chicago Midway Airport

Our best Southwest deals on Rochester to Chicago Midway Airport flight tickets
Southwest
Sep 26
ROC6:05 amGreater Rochester Intl
8h 00m
2 stops
MDW1:05 pmChicago Midway
Sep 29
MDW8:40 amChicago Midway
7h 50m
2 stops
ROC5:30 pmGreater Rochester Intl
$307
Southwest
Dec 12
ROC11:10 amGreater Rochester Intl
7h 00m
2 stops
MDW5:10 pmChicago Midway
Dec 14
MDW6:05 amChicago Midway
8h 20m
1 stop
ROC3:25 pmGreater Rochester Intl
$308
Southwest
Oct 30
ROC12:30 pmGreater Rochester Intl
8h 40m
2 stops
MDW8:10 pmChicago Midway
Nov 2
MDW4:00 pmChicago Midway
6h 40m
2 stops
ROC11:40 pmGreater Rochester Intl
$312

momondo Fare Finder

 
Customize your flight search to find flights from Rochester to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 1, 2026.
Use the filters below to find and compare flights from Rochester to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 10/21

5:55 am-12:25 pm

2 stops7h 30m

Chicago Midway

Sat 10/24

6:45 am-4:20 pm

2 stops8h 35m

$307

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 9/1

6:05 am-11:50 am

2 stops6h 45m

Chicago Midway

Tue 9/8

7:40 am-5:30 pm

2 stops8h 50m

$307

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 9/26

6:05 am-1:05 pm

2 stops8h 00m

Chicago Midway

Tue 9/29

8:40 am-5:30 pm

2 stops7h 50m

$307

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 8/26

3:20 pm-10:20 pm

2 stops8h 00m

Chicago Midway

Wed 9/2

7:40 am-5:30 pm

2 stops8h 50m

$307

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 9/16

11:55 am-7:15 pm

2 stops8h 20m

Chicago Midway

Wed 9/23

12:50 pm-9:20 pm

2 stops7h 30m

$307

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 12/12

11:10 am-5:10 pm

2 stops7h 00m

Chicago Midway

Mon 12/14

6:05 am-3:25 pm

1 stop8h 20m

$308

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 10/30

12:30 pm-8:10 pm

2 stops8h 40m

Chicago Midway

Mon 11/2

4:00 pm-11:40 pm

2 stops6h 40m

$312
Quickest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 9/17

6:45 pm-7:35 pm

Nonstop1h 50m

Chicago Midway

Sat 9/26

5:55 am-12:20 pm

1 stop5h 25m

$315

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 9/9

12:32 pm-4:57 pm

1 stop5h 25m

Chicago Midway

Sat 9/12

5:37 pm-10:54 pm

1 stop4h 17m

$325

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 10/21

6:00 am-9:17 am

1 stop4h 17m

Chicago Midway

Sat 10/24

6:44 pm-10:55 pm

1 stop3h 11m

$325

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Rochester to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Rochester. The lowest ticket price found for a Tuesday departure recently was $411. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Rochester because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $514.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Rochester in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $390 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $479. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Greater Rochester Intl to Chicago Midway flight route?

Fly from Greater Rochester Intl to Chicago Midway for the best Greater Rochester Intl - Chicago Midway flight prices

What cabin class options are available on Rochester to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Rochester to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Rochester to Chicago Midway Airport flights?

You could potentially save up to 13% on your flight if you consider stops on a Rochester to Chicago Midway Airport flight.

When to book flights from Rochester to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Rochester to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Rochester to Chicago Midway Airport (ROC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Rochester to Chicago Midway Airport

Best Price Found

$216

Fastest flight time

1h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Rochester in the past 72 hours is $216. The best round-trip flight deal from Rochester to Chicago Midway Airport found on momondo in the last 72 hours is $321.
The fastest flight from Rochester to Chicago Midway Airport takes 1h 40m
Direct flights go from Rochester to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Rochester to Chicago Midway Airport

  • How far is Greater Rochester Intl to Chicago Midway by plane?

    Greater Rochester Intl and Chicago Midway are 524.1 mi apart from one another. Typically, this will take 1h 40m by plane in normal conditions.

  • When did momondo last update prices for flights from Greater Rochester Intl Airport to Chicago Midway Airport?

    Prices for flights from Greater Rochester Intl Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Greater Rochester Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Greater Rochester Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Greater Rochester Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Rochester to Chicago Midway Airport?

  • What is the most popular airline from Rochester to Chicago Midway Airport?

Best airlines flying from Rochester to Chicago Midway Airport

Compare and see reviews for airlines that fly from Rochester to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $355Free CancellationRating
8.0
4,229 reviews
Search Southwest flights

  • Southwest Flights From Rochester to Chicago Midway Airport

    Southwest flies from Rochester to Chicago Midway Airport around 4 times per week, with 4,229 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Rochester to Chicago Midway Airport in the last 72 hours was $355 (round-trip), much lower than the average airfare cost of $489 for Southwest flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Rochester to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Rochester to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Rochester to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Rochester with this policy.

How can momondo help me find flights from Rochester to Chicago?

Once all potential Rochester to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Rochester to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Rochester and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 8/31
Mon 9/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago