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Cheap flights from Rochester to Chicago from $134

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 4/20. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:12 pm - 8:26 am
ROC
-
MDW
20h 14m
1 stop
Multiple Airlines Logo
2:15 pm - 5:40 pm
MDW
-
ROC
26h 25m
2 stops
$331Multiple Airlines
Wed, Apr 29 - Sun, May 3
Multiple Airlines Logo
8:12 pm - 8:26 am
ROC
-
MDW
13h 14m
1 stop
Multiple Airlines Logo
2:15 pm - 11:00 am
MDW
-
ROC
19h 45m
2 stops
$334Multiple Airlines
Sat, Apr 18 - Tue, Apr 21
Multiple Airlines Logo
2:02 pm - 8:26 am
ROC
-
MDW
19h 24m
1 stop
Multiple Airlines Logo
11:59 am - 11:24 am
MDW
-
ROC
46h 25m
2 stops
$338Multiple Airlines
Sat, May 2 - Sat, May 9
Southwest Logo
6:40 pm - 7:30 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
6:45 pm - 9:20 pm
MDW
-
ROC
1h 35mnonstop
$354Southwest
Tue, Apr 14 - Thu, Apr 16
Delta Logo
6:15 am - 8:47 am
ROC
-
MDW
3h 32m
1 stop
Delta Logo
6:38 pm - 11:03 pm
MDW
-
ROC
3h 25m
1 stop
$355Delta
Wed, Apr 29 - Wed, Apr 29
Multiple Airlines Logo
1:12 pm - 8:26 am
ROC
-
MDW
20h 14m
1 stop
Multiple Airlines Logo
7:30 am - 5:40 pm
MDW
-
ROC
9h 10m
2 stops
$357Multiple Airlines
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
1:12 pm - 8:26 am
ROC
-
MDW
20h 14m
1 stop
Multiple Airlines Logo
7:30 am - 5:40 pm
MDW
-
ROC
9h 10m
2 stops
$360Multiple Airlines
Wed, Apr 29 - Mon, May 4
Southwest Logo
6:40 pm - 7:30 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
11:45 am - 4:35 pm
MDW
-
ROC
3h 50m
1 stop
$364Southwest
Tue, Apr 14 - Thu, Apr 16
Southwest Logo
6:40 pm - 7:30 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
7:50 am - 4:35 pm
MDW
-
ROC
7h 45m
2 stops
$369Southwest
Tue, Apr 14 - Thu, Apr 16
Delta Logo
6:00 am - 8:53 am
ROC
-
MDW
3h 53m
1 stop
Delta Logo
6:38 pm - 11:03 pm
MDW
-
ROC
3h 25m
1 stop
$373Delta
Sat, Apr 11 - Wed, Apr 29

Southwest flights from Rochester to Chicago Midway Airport

Our best Southwest deals on Rochester to Chicago Midway Airport flight tickets
Southwest
May 31
ROC8:10 amGreater Rochester Intl
1h 50m
MDW9:00 amChicago Midway
Jun 3
MDW6:10 pmChicago Midway
1h 35m
ROC8:45 pmGreater Rochester Intl
$335
Southwest
May 31
ROC12:15 pmGreater Rochester Intl
4h 50m
1 stop
MDW4:05 pmChicago Midway
Jun 3
MDW6:10 pmChicago Midway
1h 35m
ROC8:45 pmGreater Rochester Intl
$345
Southwest
May 31
ROC8:10 amGreater Rochester Intl
1h 50m
MDW9:00 amChicago Midway
Jun 3
MDW12:45 pmChicago Midway
8h 20m
2 stops
ROC10:05 pmGreater Rochester Intl
$350

Delta flights from Rochester to Chicago Midway Airport

Our best Delta deals on Rochester to Chicago Midway Airport flight tickets
Delta
Apr 29
ROC6:15 amGreater Rochester Intl
3h 32m
1 stop
MDW8:47 amChicago Midway
May 5
MDW6:38 pmChicago Midway
3h 25m
1 stop
ROC11:03 pmGreater Rochester Intl
$355
Delta
Apr 11
ROC6:00 amGreater Rochester Intl
3h 53m
1 stop
MDW8:53 amChicago Midway
Apr 29
MDW6:38 pmChicago Midway
3h 25m
1 stop
ROC11:03 pmGreater Rochester Intl
$373
Delta
Apr 22
ROC6:15 amGreater Rochester Intl
3h 32m
1 stop
MDW8:47 amChicago Midway
Apr 25
MDW6:38 pmChicago Midway
3h 25m
1 stop
ROC11:03 pmGreater Rochester Intl
$374

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 March 23, 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 4/29

1:12 pm-8:26 am

1 stop20h 14m

Chicago Midway

Sun 5/3

2:15 pm-5:40 pm

2 stops26h 25m

$331

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 4/18

8:12 pm-8:26 am

1 stop13h 14m

Chicago Midway

Tue 4/21

2:15 pm-11:00 am

2 stops19h 45m

$334

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 5/2

2:02 pm-8:26 am

1 stop19h 24m

Chicago Midway

Sat 5/9

11:59 am-11:24 am

2 stops46h 25m

$338
Quickest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 4/14

6:40 pm-7:30 pm

Nonstop1h 50m

Chicago Midway

Thu 4/16

6:45 pm-9:20 pm

Nonstop1h 35m

$354

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 4/29

6:15 am-8:47 am

1 stop3h 32m

Chicago Midway

Wed 4/29

6:38 pm-11:03 pm

1 stop3h 25m

$355

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 4/29

1:12 pm-8:26 am

1 stop20h 14m

Chicago Midway

Mon 5/4

7:30 am-5:40 pm

2 stops9h 10m

$357

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 4/29

1:12 pm-8:26 am

1 stop20h 14m

Chicago Midway

Mon 5/4

7:30 am-5:40 pm

2 stops9h 10m

$360

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 4/14

6:40 pm-7:30 pm

Nonstop1h 50m

Chicago Midway

Thu 4/16

11:45 am-4:35 pm

1 stop3h 50m

$364

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 4/14

6:40 pm-7:30 pm

Nonstop1h 50m

Chicago Midway

Thu 4/16

7:50 am-4:35 pm

2 stops7h 45m

$369

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 4/11

6:00 am-8:53 am

1 stop3h 53m

Chicago Midway

Wed 4/29

6:38 pm-11:03 pm

1 stop3h 25m

$373

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, Monday is the cheapest day to fly to Chicago Midway Airport from Rochester. The lowest ticket price found for a Monday departure recently was $386. 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 $486.

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 $376 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?

No. A direct flight is the cheapest option for a flight between Rochester to Chicago Midway Airport.

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

$196

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 $196. The best round-trip flight deal from Rochester to Chicago Midway Airport found on momondo in the last 72 hours is $391.
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

  • 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 $305Free CancellationRating
8.0
4,324 reviews
Search Southwest flights

  • Southwest Flights From Rochester to Chicago Midway Airport

    Southwest flies from Rochester to Chicago Midway Airport around 12 times per week, with 4,324 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Rochester to Chicago Midway Airport in the last 72 hours was $305 (round-trip), much lower than the average airfare cost of $391 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
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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