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Cheap flights from Rochester to Chicago from $95

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 1/11. 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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Multiple Airlines Logo
12:33 pm - 11:29 pmROC-MDW
11h 56m1 stop
Multiple Airlines Logo
5:30 pm - 11:38 amMDW-ROC
17h 08m1 stop
$300Multiple Airlines
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Fri, Nov 21 - Sun, Nov 23
Delta Logo
6:00 am - 5:55 pmROC-MDW
12h 55m1 stop
Delta Logo
1:28 pm - 10:54 pmMDW-ROC
8h 26m1 stop
$305Delta
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Wed, Jan 21 - Tue, Jan 27
Multiple Airlines Logo
6:57 pm - 10:26 amROC-MDW
16h 29m2 stops
Multiple Airlines Logo
9:27 am - 5:30 pmMDW-ROC
7h 03m1 stop
$332Multiple Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Multiple Airlines Logo
6:00 pm - 9:58 pmROC-MDW
28h 58m1 stop
Multiple Airlines Logo
9:43 pm - 6:10 pmMDW-ROC
19h 27m2 stops
$335Multiple Airlines
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Sun, Dec 21 - Sun, Jan 18
Southwest Logo
6:30 pm - 7:25 pmROC-MDW
1h 55mnonstop
Southwest Logo
3:15 pm - 5:50 pmMDW-ROC
1h 35mnonstop
$336Southwest
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Mon, Dec 8 - Wed, Dec 10
Delta Logo
6:00 am - 8:54 amROC-MDW
3h 54m1 stop
Delta Logo
6:35 pm - 10:54 pmMDW-ROC
3h 19m1 stop
$339Delta
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Tue, Jan 27 - Tue, Jan 27
Southwest Logo
12:00 pm - 4:20 pmROC-MDW
5h 20m1 stop
Southwest Logo
3:15 pm - 5:50 pmMDW-ROC
1h 35mnonstop
$346Southwest
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Sat, Dec 6 - Tue, Dec 9
Multiple Airlines Logo
12:14 pm - 12:30 amROC-MDW
13h 16m2 stops
Multiple Airlines Logo
5:30 pm - 11:38 amMDW-ROC
17h 08m1 stop
$349Multiple Airlines
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Sun, Nov 16 - Thu, Nov 20
Southwest Logo
6:00 am - 2:05 pmROC-MDW
9h 05m2 stops
Southwest Logo
3:15 pm - 5:50 pmMDW-ROC
1h 35mnonstop
$351Southwest
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Sat, Dec 6 - Tue, Dec 9
Southwest Logo
6:30 pm - 7:25 pmROC-MDW
1h 55mnonstop
Southwest Logo
3:15 pm - 5:50 pmMDW-ROC
1h 35mnonstop
$353Southwest
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Thu, Dec 4 - Mon, Dec 8

Southwest flights from Rochester to Chicago Midway Airport

Our best Southwest deals on Rochester to Chicago Midway Airport flight tickets
Southwest
Dec 8
ROC6:30 pmGreater Rochester Intl
1h 55m
MDW7:25 pmChicago Midway
Dec 10
MDW3:15 pmChicago Midway
1h 35m
ROC5:50 pmGreater Rochester Intl
$336
Find similar
Southwest
Dec 6
ROC12:00 pmGreater Rochester Intl
5h 20m
1 stop
MDW4:20 pmChicago Midway
Dec 9
MDW3:15 pmChicago Midway
1h 35m
ROC5:50 pmGreater Rochester Intl
$346
Find similar
Southwest
Dec 6
ROC6:00 amGreater Rochester Intl
9h 05m
2 stops
MDW2:05 pmChicago Midway
Dec 9
MDW3:15 pmChicago Midway
1h 35m
ROC5:50 pmGreater Rochester Intl
$351
Find similar

Delta flights from Rochester to Chicago Midway Airport

Our best Delta deals on Rochester to Chicago Midway Airport flight tickets
Delta
Jan 21
ROC6:00 amGreater Rochester Intl
12h 55m
1 stop
MDW5:55 pmChicago Midway
Jan 27
MDW1:28 pmChicago Midway
8h 26m
1 stop
ROC10:54 pmGreater Rochester Intl
$305
Find similar
Delta
Jan 27
ROC6:00 amGreater Rochester Intl
3h 54m
1 stop
MDW8:54 amChicago Midway
Jan 27
MDW6:35 pmChicago Midway
3h 19m
1 stop
ROC10:54 pmGreater Rochester Intl
$339
Find similar
Delta
Jan 24
ROC6:00 amGreater Rochester Intl
3h 54m
1 stop
MDW8:54 amChicago Midway
Jan 24
MDW4:30 pmChicago Midway
6h 29m
1 stop
ROC11:59 pmGreater Rochester Intl
$373
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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 November 3, 2025.
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

Fri 11/21

12:33 pm-11:29 pm

1 stop11h 56m

Chicago Midway

Sun 11/23

5:30 pm-11:38 am

1 stop17h 08m

$300

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 1/21

6:00 am-5:55 pm

1 stop12h 55m

Chicago Midway

Tue 1/27

1:28 pm-10:54 pm

1 stop8h 26m

$305

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 11/14

6:57 pm-10:26 am

2 stops16h 29m

Chicago Midway

Mon 11/17

9:27 am-5:30 pm

1 stop7h 03m

$332

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 12/21

6:00 pm-9:58 pm

1 stop28h 58m

Chicago Midway

Sun 1/18

9:43 pm-6:10 pm

2 stops19h 27m

$335

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 12/8

6:30 pm-7:25 pm

Nonstop1h 55m

Chicago Midway

Wed 12/10

3:15 pm-5:50 pm

Nonstop1h 35m

$336

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 1/27

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Tue 1/27

6:35 pm-10:54 pm

1 stop3h 19m

$339

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 12/6

12:00 pm-4:20 pm

1 stop5h 20m

Chicago Midway

Tue 12/9

3:15 pm-5:50 pm

Nonstop1h 35m

$346

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 11/16

12:14 pm-12:30 am

2 stops13h 16m

Chicago Midway

Thu 11/20

5:30 pm-11:38 am

1 stop17h 08m

$349

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 12/6

6:00 am-2:05 pm

2 stops9h 05m

Chicago Midway

Tue 12/9

3:15 pm-5:50 pm

Nonstop1h 35m

$351

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 12/4

6:30 pm-7:25 pm

Nonstop1h 55m

Chicago Midway

Mon 12/8

3:15 pm-5:50 pm

Nonstop1h 35m

$353

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 $312. 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 $502.

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 $329 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.

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

$156

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Rochester in the past 72 hours is $156. The best round-trip flight deal from Rochester to Chicago Midway Airport found on momondo in the last 72 hours is $334.
The fastest flight from Rochester to Chicago Midway Airport takes 1h 50m
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 55m 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
4,238 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 4,238 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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Hammond
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Munster
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Porter
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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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