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Cheap flights from Rochester to Chicago from $105

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 10/31. 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

Multiple Airlines Logo
1:13 pm - 10:10 pmROC-MDW
9h 57m1 stop
Multiple Airlines Logo
9:27 am - 12:17 pmMDW-ROC
25h 50m1 stop
$226Multiple Airlines
Find Deal
vie., nov. 14 - lun., nov. 17
Multiple Airlines Logo
6:57 pm - 10:21 amROC-MDW
16h 24m2 stops
Multiple Airlines Logo
10:13 am - 8:48 pmMDW-ROC
9h 35m1 stop
$244Multiple Airlines
Find Deal
vie., oct. 3 - dom., oct. 5
Multiple Airlines Logo
6:57 pm - 10:26 amROC-MDW
16h 29m2 stops
Multiple Airlines Logo
7:50 am - 11:00 amMDW-ROC
26h 10m1 stop
$255Multiple Airlines
Find Deal
vie., oct. 31 - vie., nov. 7
Southwest Logo
7:55 am - 8:45 amROC-MDW
1h 50mnonstop
Southwest Logo
6:55 pm - 9:30 pmMDW-ROC
1h 35mnonstop
$311Southwest
Find Deal
jue., oct. 23 - lun., oct. 27
Delta Logo
1:15 pm - 6:34 pmROC-MDW
6h 19m1 stop
Delta Logo
10:35 am - 5:33 pmMDW-ROC
5h 58m1 stop
$319Delta
Find Deal
dom., feb. 1 - jue., feb. 5
Southwest Logo
6:45 pm - 7:35 pmROC-MDW
1h 50mnonstop
Southwest Logo
6:00 am - 12:20 pmMDW-ROC
5h 20m1 stop
$321Southwest
Find Deal
mié., oct. 15 - sáb., oct. 18
Southwest Logo
6:45 pm - 7:35 pmROC-MDW
1h 50mnonstop
Southwest Logo
1:15 pm - 10:25 pmMDW-ROC
8h 10m2 stops
$326Southwest
Find Deal
mar., oct. 28 - mié., oct. 29
Delta Logo
6:21 pm - 11:32 pmROC-MDW
6h 11m1 stop
Delta Logo
9:34 am - 4:33 pmMDW-ROC
5h 59m1 stop
$331Delta
Find Deal
mar., dic. 2 - lun., dic. 8
Southwest Logo
6:45 pm - 7:35 pmROC-MDW
1h 50mnonstop
Southwest Logo
6:55 pm - 9:30 pmMDW-ROC
1h 35mnonstop
$332Southwest
Find Deal
mié., oct. 22 - vie., oct. 24
Delta Logo
12:30 pm - 6:25 pmROC-MDW
6h 55m1 stop
Delta Logo
6:23 pm - 11:30 amMDW-ROC
16h 07m1 stop
$336Delta
Find Deal
jue., oct. 16 - lun., oct. 20

Delta flights from Rochester to Chicago Midway Airport

Our best Delta deals on Rochester to Chicago Midway Airport flight tickets
Delta
Feb 1
ROC1:15 pmRochester Greater Rochester Intl
6h 19m
1 stop
MDW6:34 pmChicago Midway
Feb 5
MDW10:35 amChicago Midway
5h 58m
1 stop
ROC5:33 pmRochester Greater Rochester Intl
$319
Find similar
Delta
Dec 2
ROC6:21 pmRochester Greater Rochester Intl
6h 11m
1 stop
MDW11:32 pmChicago Midway
Dec 8
MDW9:34 amChicago Midway
5h 59m
1 stop
ROC4:33 pmRochester Greater Rochester Intl
$331
Find similar
Delta
Oct 16
ROC12:30 pmRochester Greater Rochester Intl
6h 55m
1 stop
MDW6:25 pmChicago Midway
Oct 20
MDW6:23 pmChicago Midway
16h 07m
1 stop
ROC11:30 amRochester Greater Rochester Intl
$336
Find similar

Southwest flights from Rochester to Chicago Midway Airport

Our best Southwest deals on Rochester to Chicago Midway Airport flight tickets
Southwest
Oct 23
ROC7:55 amRochester Greater Rochester Intl
1h 50m
MDW8:45 amChicago Midway
Oct 27
MDW6:55 pmChicago Midway
1h 35m
ROC9:30 pmRochester Greater Rochester Intl
$311
Find similar
Southwest
Oct 15
ROC6:45 pmRochester Greater Rochester Intl
1h 50m
MDW7:35 pmChicago Midway
Oct 18
MDW6:00 amChicago Midway
5h 20m
1 stop
ROC12:20 pmRochester Greater Rochester Intl
$321
Find similar
Southwest
Oct 28
ROC6:45 pmRochester Greater Rochester Intl
1h 50m
MDW7:35 pmChicago Midway
Oct 29
MDW1:15 pmChicago Midway
8h 10m
2 stops
ROC10:25 pmRochester Greater Rochester Intl
$326
Find similar

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 septiembre 16, 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

Rochester Greater Rochester Intl

vie. 11/14

1:13 pm-10:10 pm

1 stop9h 57m

Chicago Midway

lun. 11/17

9:27 am-12:17 pm

1 stop25h 50m

$226

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

vie. 10/3

6:57 pm-10:21 am

2 stops16h 24m

Chicago Midway

dom. 10/5

10:13 am-8:48 pm

1 stop9h 35m

$244

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

vie. 10/31

6:57 pm-10:26 am

2 stops16h 29m

Chicago Midway

vie. 11/7

7:50 am-11:00 am

1 stop26h 10m

$255

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

jue. 10/23

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

lun. 10/27

6:55 pm-9:30 pm

Nonstop1h 35m

$311

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

dom. 2/1

1:15 pm-6:34 pm

1 stop6h 19m

Chicago Midway

jue. 2/5

10:35 am-5:33 pm

1 stop5h 58m

$319

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

mié. 10/15

6:45 pm-7:35 pm

Nonstop1h 50m

Chicago Midway

sáb. 10/18

6:00 am-12:20 pm

1 stop5h 20m

$321

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

mar. 10/28

6:45 pm-7:35 pm

Nonstop1h 50m

Chicago Midway

mié. 10/29

1:15 pm-10:25 pm

2 stops8h 10m

$326

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

mar. 12/2

6:21 pm-11:32 pm

1 stop6h 11m

Chicago Midway

lun. 12/8

9:34 am-4:33 pm

1 stop5h 59m

$331

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

mié. 10/22

6:45 pm-7:35 pm

Nonstop1h 50m

Chicago Midway

vie. 10/24

6:55 pm-9:30 pm

Nonstop1h 35m

$332

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

jue. 10/16

12:30 pm-6:25 pm

1 stop6h 55m

Chicago Midway

lun. 10/20

6:23 pm-11:30 am

1 stop16h 07m

$336

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 $304. 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 $320 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 Rochester Greater Rochester Intl to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Rochester 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

$174

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 $174. The best round-trip flight deal from Rochester to Chicago Midway Airport found on momondo in the last 72 hours is $322.
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 Rochester Greater Rochester Intl to Chicago Midway by plane?

    Rochester Greater Rochester Intl and Chicago Midway are 524.1 mi apart from one another. Typically, this will take 1h 50m by plane in normal conditions.

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

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

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

  • How old do you have to be to fly from Rochester 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 Rochester 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 $287Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Rochester to Chicago Midway Airport

    Southwest flies from Rochester to Chicago Midway Airport around 5 times per week, with 4,242 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Rochester to Chicago Midway Airport in the last 72 hours was $287 (round-trip), much lower than the average airfare cost of $381 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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