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$90+ Cheap flights from Rochester (ROC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — MDW
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Cheap flight deals from Rochester to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Rochester (ROC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$273
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

October

Cheapest in

November

Average price

$592

Good round-trip deal

$298 or less

Good one-way deal

$162 or less
Provider with most accurate pricing for Greater Rochester Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Greater Rochester Intl-Chicago Midway flights.
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From Greater Rochester Intl to Chicago Midway
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One-way flight from Greater Rochester Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($73 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Greater Rochester Intl to Chicago Midway.
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Price to beat on a one-way flight from Greater Rochester Intl to Chicago Midway.
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Find flight deals from Rochester to Midway

Cheapest flights from Rochester to Midway
Explore the most affordable flight options available from Rochester to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:57 pmROC - MDW
2 stops24h 42mMultiple Airlines
Mon 11/108:00 amMDW - ROC
1 stop8h 30mMultiple Airlines
Deal found 10/19$273
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:17 amROC - MDW
1 stop3h 37mDelta
Thu 11/139:34 amMDW - ROC
1 stop6h 00mDelta
Deal found 10/18$294
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:00 amROC - MDW
1 stop6h 52mDelta
Mon 11/175:34 pmMDW - ROC
1 stop5h 18mDelta
Deal found 10/19$319
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:17 amROC - MDW
1 stop3h 32mDelta
Sun 12/79:34 amMDW - ROC
1 stop5h 59mDelta
Deal found 10/18$324
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:30 pmROC - MDW
Nonstop1h 55mSouthwest
Thu 11/2711:50 amMDW - ROC
1 stop3h 50mSouthwest
Deal found 10/19$330
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:30 pmROC - MDW
Nonstop1h 55mSouthwest
Sun 11/167:30 pmMDW - ROC
Nonstop1h 35mSouthwest
Deal found 10/18$331
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:30 pmROC - MDW
1 stop7h 05mSouthwest
Sun 12/76:45 amMDW - ROC
2 stops9h 15mSouthwest
Deal found 10/18$334
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:14 pmROC - MDW
2 stops29h 43mMultiple Airlines
Mon 11/179:27 amMDW - ROC
1 stop7h 03mMultiple Airlines
Deal found 10/18$347

Cheapflights Fare Finder

 
Customize your flight search to find flights from Rochester to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated October 20, 2025.
Use the filters below to find and compare flights from Rochester to Chicago Midway Airport that are best for you.

Fly from

Rochester

Fly to

Midway

Route

Depart

Return

Price

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 11/7

6:57 pm-6:39 pm

2 stops24h 42m

Chicago Midway

Mon 11/10

8:00 am-5:30 pm

1 stop8h 30m

$273

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 1/31

12:55 pm-6:40 pm

1 stop6h 45m

Chicago Midway

Fri 2/6

6:10 pm-8:45 pm

Nonstop1h 35m

$284

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 11/11

6:17 am-8:54 am

1 stop3h 37m

Chicago Midway

Thu 11/13

9:34 am-4:34 pm

1 stop6h 00m

$294

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 1/22

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

Sun 1/25

6:10 pm-8:45 pm

Nonstop1h 35m

$299

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 12/6

6:17 am-8:49 am

1 stop3h 32m

Chicago Midway

Sun 12/7

9:34 am-4:33 pm

1 stop5h 59m

$324

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 11/18

6:30 pm-7:25 pm

Nonstop1h 55m

Chicago Midway

Thu 11/27

11:50 am-4:40 pm

1 stop3h 50m

$330

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 12/6

4:30 pm-10:35 pm

1 stop7h 05m

Chicago Midway

Sun 12/7

6:45 am-5:00 pm

2 stops9h 15m

$334

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 11/19

6:30 pm-7:25 pm

Nonstop1h 55m

$125

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 1/21

6:10 am-7:25 am

Nonstop2h 15m

$125

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 1/14

1:15 pm-6:34 pm

1 stop6h 19m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 17 results
1
2

Compare providers for flights from Rochester to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Rochester to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Rochester-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Rochester-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Rochester-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Rochester-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Rochester-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Rochester to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Rochester with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Rochester to Chicago Midway Airport

What is the cheapest month to book a flight from Rochester to Chicago Midway Airport?

Currently, November is the cheapest month in which you can book a flight from Rochester to Chicago Midway Airport (average of $129). Flying from Rochester to Chicago Midway Airport in April is currently the most expensive (average of $302). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ROC to MDW?

Find hourly flight availability from Rochester to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2025.

When flying from Rochester to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 28% versus a flight at noon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated October 20, 2025.
Read reviews from past customers who have flown Southwest from Rochester to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Rochester to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Rochester to Chicago Midway?

    Located just 3.8 mi from the city center, Greater Rochester Intl is the airport most travelers will use when flying to Chicago Midway from Rochester. Booking flights from Greater Rochester Intl (ROC) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 1 airline.

  • How long is the flight from Rochester to Chicago Midway Airport?

    A quick flight from Rochester to Chicago Midway Airport can take about 3h 37m. Southwest provides one of the quickest options available for as low as $294. The distance from Rochester to Chicago Midway Airport is about 521 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Rochester to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($287), offers the cheapest pricing from Rochester to Chicago Midway Airport. This flight start at 28% lower than the current average price 3 months from now.

  • What are the cheapest flights from Rochester to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $120. While the most popular route (Greater Rochester Intl - Chicago Midway) can be booked for $257 on average, our data indicates $299 when flying from Rochester to Chicago Midway Airport.

  • Can I find deals for flights from Rochester to Midway that include hotel bookings?

    Yes. In addition to deals on Rochester to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Rochester to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Rochester to Midway.

  • Can I find deals for business class flights from Rochester to Midway?

    Yes. Cheapflights offers flight deals from Rochester to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Rochester to Chicago Midway Airport?

    Currently, November is the cheapest month in which you can book a flight from Rochester to Chicago Midway Airport (average of $129). Flying from Rochester to Chicago Midway Airport in April is currently the most expensive (average of $302). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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Alternative routes for Rochester to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Rochester to Midway

Discover the top airline that operate flights from Rochester to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$287Average$393FlexibilityNo cancel feeOn-time63%

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