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Cheap flights from Rochester to Chicago from $120

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 5/27. 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
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
8:05 am - 8:55 am
ROC
-
MDW
1h 50mnonstop
Southwest Logo
6:30 pm - 9:05 pm
MDW
-
ROC
1h 35mnonstop
$335Southwest
Tue, Jun 2 - Tue, Jun 9
Delta Logo
6:10 am - 9:14 am
ROC
-
MDW
4h 04m
1 stop
Delta Logo
6:00 am - 1:10 pm
MDW
-
ROC
6h 10m
1 stop
$345Delta
Wed, Jun 17 - Sat, Jun 20
Southwest Logo
8:05 am - 8:55 am
ROC
-
MDW
1h 50mnonstop
Southwest Logo
1:00 pm - 10:45 pm
MDW
-
ROC
8h 45m
2 stops
$350Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
6:40 pm - 7:30 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
3:35 pm - 6:05 pm
MDW
-
ROC
1h 30mnonstop
$354Southwest
Wed, May 27 - Sat, May 30
Delta Logo
6:00 am - 10:00 am
ROC
-
MDW
5h 00m
1 stop
Delta Logo
9:22 am - 3:20 pm
MDW
-
ROC
4h 58m
1 stop
$355Delta
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
12:35 pm - 7:25 pm
ROC
-
MDW
7h 50m
2 stops
Southwest Logo
5:30 pm - 10:45 pm
MDW
-
ROC
4h 15m
1 stop
$360Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
6:45 pm - 7:35 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
8:30 am - 11:15 am
MDW
-
ROC
1h 45mnonstop
$364Southwest
Mon, Sep 14 - Wed, Sep 16
Southwest Logo
6:20 pm - 7:05 pm
ROC
-
MDW
1h 45mnonstop
Southwest Logo
3:05 pm - 9:15 pm
MDW
-
ROC
5h 10m
1 stop
$365Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
6:35 am - 1:30 pm
ROC
-
MDW
7h 55m
2 stops
Southwest Logo
1:00 pm - 10:45 pm
MDW
-
ROC
8h 45m
2 stops
$366Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
6:40 pm - 7:30 pm
ROC
-
MDW
1h 50mnonstop
Southwest Logo
8:35 am - 4:20 pm
MDW
-
ROC
6h 45m
2 stops
$369Southwest
Wed, May 27 - Sat, May 30

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Delta flights from Rochester to Chicago Midway Airport

Our best Delta deals on Rochester to Chicago Midway Airport flight tickets
Delta
Jun 17
ROC6:10 amGreater Rochester Intl
4h 04m
1 stop
MDW9:14 amChicago Midway
Jun 20
MDW6:00 amChicago Midway
6h 10m
1 stop
ROC1:10 pmGreater Rochester Intl
$345
Delta
Jun 2
ROC6:00 amGreater Rochester Intl
5h 00m
1 stop
MDW10:00 amChicago Midway
Jun 3
MDW9:22 amChicago Midway
4h 58m
1 stop
ROC3:20 pmGreater Rochester Intl
$355
Delta
May 30
ROC6:00 amGreater Rochester Intl
4h 59m
1 stop
MDW9:59 amChicago Midway
Jun 3
MDW5:15 pmChicago Midway
5h 42m
1 stop
ROC11:57 pmGreater Rochester Intl
$374

Southwest flights from Rochester to Chicago Midway Airport

Our best Southwest deals on Rochester to Chicago Midway Airport flight tickets
Southwest
Jun 2
ROC8:05 amGreater Rochester Intl
1h 50m
MDW8:55 amChicago Midway
Jun 9
MDW6:30 pmChicago Midway
1h 35m
ROC9:05 pmGreater Rochester Intl
$335
Southwest
Jun 2
ROC8:05 amGreater Rochester Intl
1h 50m
MDW8:55 amChicago Midway
Jun 9
MDW1:00 pmChicago Midway
8h 45m
2 stops
ROC10:45 pmGreater Rochester Intl
$350
Southwest
May 28
ROC7:50 amGreater Rochester Intl
1h 50m
MDW8:40 amChicago Midway
Jun 10
MDW1:10 pmChicago Midway
1h 35m
ROC3:45 pmGreater Rochester Intl
$354

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 May 7, 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

Tue 6/2

8:05 am-8:55 am

Nonstop1h 50m

Chicago Midway

Tue 6/9

6:30 pm-9:05 pm

Nonstop1h 35m

$335

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 6/17

6:10 am-9:14 am

1 stop4h 04m

Chicago Midway

Sat 6/20

6:00 am-1:10 pm

1 stop6h 10m

$345

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 6/2

8:05 am-8:55 am

Nonstop1h 50m

Chicago Midway

Tue 6/9

1:00 pm-10:45 pm

2 stops8h 45m

$350
Quickest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 5/27

6:40 pm-7:30 pm

Nonstop1h 50m

Chicago Midway

Sat 5/30

3:35 pm-6:05 pm

Nonstop1h 30m

$354

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 6/2

6:00 am-10:00 am

1 stop5h 00m

Chicago Midway

Wed 6/3

9:22 am-3:20 pm

1 stop4h 58m

$355

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 6/2

12:35 pm-7:25 pm

2 stops7h 50m

Chicago Midway

Tue 6/9

5:30 pm-10:45 pm

1 stop4h 15m

$360

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 9/14

6:45 pm-7:35 pm

Nonstop1h 50m

Chicago Midway

Wed 9/16

8:30 am-11:15 am

Nonstop1h 45m

$364

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 9/16

6:20 pm-7:05 pm

Nonstop1h 45m

Chicago Midway

Tue 9/22

3:05 pm-9:15 pm

1 stop5h 10m

$365

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 6/2

6:35 am-1:30 pm

2 stops7h 55m

Chicago Midway

Tue 6/9

1:00 pm-10:45 pm

2 stops8h 45m

$366

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 5/27

6:40 pm-7:30 pm

Nonstop1h 50m

Chicago Midway

Sat 5/30

8:35 am-4:20 pm

2 stops6h 45m

$369

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, Tuesday is the cheapest day to fly to Chicago Midway Airport from Rochester. The lowest ticket price found for a Tuesday departure recently was $404. 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 $517.

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 $393 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $464. 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

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

$205

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 $205. The best round-trip flight deal from Rochester to Chicago Midway Airport found on momondo in the last 72 hours is $406.
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

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 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 $305Free CancellationRating
7.9
4,301 reviews
Search Southwest flights

  • Southwest Flights From Rochester to Chicago Midway Airport

    Southwest flies from Rochester to Chicago Midway Airport around 10 times per week, with 4,301 momondo users rating the airline 7.9/10. 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 $411 for Southwest flights on this route.

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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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