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Cheap flights from Rochester to Chicago from $106

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 2/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:50 pm - 8:40 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
3:35 pm - 6:05 pm
MDW
-
ROC
1h 30mnonstop
$315Southwest
Thu, Apr 16 - Sat, Apr 18
Southwest Logo
4:00 pm - 10:20 pm
ROC
-
MDW
7h 20m
1 stop
Southwest Logo
3:35 pm - 6:05 pm
MDW
-
ROC
1h 30mnonstop
$325Southwest
Thu, Apr 16 - Sat, Apr 18
Southwest Logo
12:40 pm - 8:35 pm
ROC
-
MDW
8h 55m
2 stops
Southwest Logo
3:35 pm - 6:05 pm
MDW
-
ROC
1h 30mnonstop
$330Southwest
Thu, Apr 16 - Sat, Apr 18
Southwest Logo
6:35 pm - 7:45 pm
ROC
-
MDW
2h 10mnonstop
Southwest Logo
2:15 pm - 4:50 pm
MDW
-
ROC
1h 35mnonstop
$335Southwest
Mon, Feb 23 - Sat, Feb 28
Southwest Logo
4:55 pm - 8:40 pm
ROC
-
MDW
4h 45m
1 stop
Southwest Logo
2:35 pm - 10:05 pm
MDW
-
ROC
6h 30m
2 stops
$340Southwest
Sat, May 16 - Tue, May 19
Southwest Logo
6:35 pm - 7:45 pm
ROC
-
MDW
2h 10mnonstop
Southwest Logo
7:30 am - 2:40 pm
MDW
-
ROC
6h 10m
1 stop
$345Southwest
Mon, Feb 23 - Sat, Feb 28
Southwest Logo
12:45 pm - 7:35 pm
ROC
-
MDW
7h 50m
2 stops
Southwest Logo
2:15 pm - 4:50 pm
MDW
-
ROC
1h 35mnonstop
$350Southwest
Mon, Feb 23 - Sat, Feb 28
Southwest Logo
3:25 pm - 10:15 pm
ROC
-
MDW
7h 50m
1 stop
Southwest Logo
9:10 am - 4:40 pm
MDW
-
ROC
6h 30m
1 stop
$351Southwest
Sat, May 16 - Tue, May 19
Southwest Logo
8:10 am - 9:00 am
ROC
-
MDW
1h 50mnonstop
Southwest Logo
12:45 pm - 3:20 pm
MDW
-
ROC
1h 35mnonstop
$353Southwest
Sun, Apr 26 - Wed, Apr 29
Southwest Logo
7:50 pm - 8:40 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
12:45 pm - 3:15 pm
MDW
-
ROC
1h 30mnonstop
$355Southwest
Thu, Mar 12 - Sat, Mar 14

Southwest flights from Rochester to Chicago Midway Airport

Our best Southwest deals on Rochester to Chicago Midway Airport flight tickets
Southwest
May 7
ROC7:50 pmGreater Rochester Intl
1h 50m
MDW8:40 pmChicago Midway
May 11
MDW6:45 pmChicago Midway
1h 35m
ROC9:20 pmGreater Rochester Intl
$315
Southwest
May 7
ROC4:00 pmGreater Rochester Intl
7h 20m
1 stop
MDW10:20 pmChicago Midway
May 11
MDW6:45 pmChicago Midway
1h 35m
ROC9:20 pmGreater Rochester Intl
$325
Southwest
May 7
ROC7:50 pmGreater Rochester Intl
1h 50m
MDW8:40 pmChicago Midway
May 11
MDW2:10 pmChicago Midway
8h 00m
2 stops
ROC11:10 pmGreater Rochester Intl
$330

Delta flights from Rochester to Chicago Midway Airport

Our best Delta deals on Rochester to Chicago Midway Airport flight tickets
Delta
Apr 30
ROC10:09 amGreater Rochester Intl
3h 34m
1 stop
MDW12:43 pmChicago Midway
May 3
MDW6:00 amChicago Midway
4h 53m
1 stop
ROC11:53 amGreater Rochester Intl
$373
Delta
Mar 26
ROC10:09 amGreater Rochester Intl
3h 20m
1 stop
MDW12:29 pmChicago Midway
Mar 29
MDW9:35 amChicago Midway
5h 07m
1 stop
ROC3:42 pmGreater Rochester Intl
$411
Delta
Feb 26
ROC6:05 amGreater Rochester Intl
6h 54m
1 stop
MDW11:59 amChicago Midway
Mar 2
MDW6:00 amChicago Midway
5h 04m
1 stop
ROC12:04 pmGreater Rochester Intl
$433

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 February 3, 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

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 4/16

7:50 pm-8:40 pm

Nonstop1h 50m

Chicago Midway

Sat 4/18

3:35 pm-6:05 pm

Nonstop1h 30m

$315

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 4/16

4:00 pm-10:20 pm

1 stop7h 20m

Chicago Midway

Sat 4/18

3:35 pm-6:05 pm

Nonstop1h 30m

$325

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 4/16

12:40 pm-8:35 pm

2 stops8h 55m

Chicago Midway

Sat 4/18

3:35 pm-6:05 pm

Nonstop1h 30m

$330

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 2/23

6:35 pm-7:45 pm

Nonstop2h 10m

Chicago Midway

Sat 2/28

2:15 pm-4:50 pm

Nonstop1h 35m

$335

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 5/16

4:55 pm-8:40 pm

1 stop4h 45m

Chicago Midway

Tue 5/19

2:35 pm-10:05 pm

2 stops6h 30m

$340

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 2/23

6:35 pm-7:45 pm

Nonstop2h 10m

Chicago Midway

Sat 2/28

7:30 am-2:40 pm

1 stop6h 10m

$345

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 2/23

12:45 pm-7:35 pm

2 stops7h 50m

Chicago Midway

Sat 2/28

2:15 pm-4:50 pm

Nonstop1h 35m

$350

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 5/16

3:25 pm-10:15 pm

1 stop7h 50m

Chicago Midway

Tue 5/19

9:10 am-4:40 pm

1 stop6h 30m

$351

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 4/26

8:10 am-9:00 am

Nonstop1h 50m

Chicago Midway

Wed 4/29

12:45 pm-3:20 pm

Nonstop1h 35m

$353

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 3/12

7:50 pm-8:40 pm

Nonstop1h 50m

Chicago Midway

Sat 3/14

12:45 pm-3:15 pm

Nonstop1h 30m

$355

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Rochester. The lowest ticket price found for a Wednesday departure recently was $362. 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 $477.

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 $350 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $446. 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 Greater Rochester Intl to Chicago Midway flights?

There is only 1 cabin class available to choose from on Greater Rochester Intl to Chicago Midway 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 23% 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

$148

Fastest flight time

1h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Rochester in the past 72 hours is $148. The best round-trip flight deal from Rochester to Chicago Midway Airport found on momondo in the last 72 hours is $353.
The fastest flight from Rochester to Chicago Midway Airport takes 1h 45m
Direct flights go from Rochester to Chicago Midway Airport every day.
Search flight deals

  • 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 45m 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 $303Free CancellationRating
8.0
4,272 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 4,272 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Rochester to Chicago Midway Airport in the last 72 hours was $303 (round-trip), much lower than the average airfare cost of $393 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
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New Buffalo
Hammond
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Portage
Lansing
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Valparaiso
Munster
Crown Point
Chesterton
Monticello
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

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