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Midway

$59+ Cheap flights from Minneapolis (MSP) 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Minneapolis St Paul to Chicago Midway are usually found in September or October, booked 65 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Minneapolis to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Minneapolis (MSP) 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 August 14, 2025.

Round-trip from

$92
(Southwest)

One-way from

$59
(Southwest)

Popular in

March

Cheapest in

September

Average price

$190

Good round-trip deal

$133 or less

Good one-way deal

$155 or less
From Minneapolis St Paul to Chicago Midway
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One-way flight from Minneapolis St Paul to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Minneapolis St Paul to Chicago Midway.
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Price to beat on a one-way flight from Minneapolis St Paul to Chicago Midway.
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Find flight deals from Minneapolis to Midway

Cheapest flights from Minneapolis to Midway
Explore the most affordable flight options available from Minneapolis to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 9/46:35 amMSP - MDW
2 stops6h 55mSouthwest
Sat 9/610:35 amMDW - MSP
Nonstop1h 35mSouthwest
Deal found 8/14$92
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 9/43:30 pmMSP - MDW
1 stop8h 35mSouthwest
Mon 9/85:25 pmMDW - MSP
Nonstop1h 35mSouthwest
Deal found 8/14$93
This Southwest deal was found by Cheapflights users on 8/12. 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 9/96:20 amMSP - MDW
1 stop7h 25mSouthwest
Tue 9/169:00 amMDW - MSP
1 stop5h 30mSouthwest
Deal found 8/12$97
This Southwest deal was found by Cheapflights users on 8/14. 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.
Sun 9/215:05 amMSP - MDW
Nonstop1h 25mSouthwest
Mon 9/2212:10 pmMDW - MSP
Nonstop1h 35mSouthwest
Deal found 8/14$100
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 10/236:40 amMSP - MDW
2 stops6h 40mSouthwest
Sat 10/258:20 amMDW - MSP
2 stops8h 15mSouthwest
Deal found 8/12$107
This Southwest deal was found by Cheapflights users on 8/13. 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 9/207:20 amMSP - MDW
Nonstop1h 30mSouthwest
Sat 9/203:10 pmMDW - MSP
Nonstop1h 35mSouthwest
Deal found 8/13$109
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/59:55 amMSP - MDW
Nonstop1h 25mSouthwest
Mon 9/85:25 pmMDW - MSP
Nonstop1h 35mSouthwest
Deal found 8/14$110
This Southwest deal was found by Cheapflights users on 8/14. 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.
Wed 9/108:50 amMSP - MDW
2 stops8h 55mSouthwest
Sun 9/1410:25 pmMDW - MSP
Nonstop1h 40mSouthwest
Deal found 8/14$115
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 10/96:00 amMSP - MDW
1 stop9h 15mSouthwest
Sun 10/129:15 amMDW - MSP
Nonstop1h 30mSouthwest
Deal found 8/13$116
This Delta deal was found by Cheapflights users on 8/11. 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.
Wed 9/37:13 amMSP - MDW
Nonstop1h 37mDelta
Wed 9/37:17 pmMDW - MSP
Nonstop1h 43mDelta
Deal found 8/11$117

Cheapflights Fare Finder

 
Customize your flight search to find flights from Minneapolis 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 August 14, 2025.
Use the filters below to find and compare flights from Minneapolis to Chicago Midway Airport that are best for you.

Fly from

Minneapolis

Fly to

Midway

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 9/10

8:50 am-5:45 pm

2 stops8h 55m

Chicago Midway

Wed 9/17

8:30 am-10:05 am

Nonstop1h 35m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 9/3

6:35 am-1:25 pm

2 stops6h 50m

Chicago Midway

Wed 9/3

4:25 pm-6:00 pm

Nonstop1h 35m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 9/16

6:35 am-1:25 pm

2 stops6h 50m

Chicago Midway

Tue 9/16

8:20 pm-9:55 pm

Nonstop1h 35m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 10/23

6:40 am-1:20 pm

2 stops6h 40m

Chicago Midway

Sat 10/25

9:50 am-11:20 am

Nonstop1h 30m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 9/4

6:35 am-1:30 pm

2 stops6h 55m

Chicago Midway

Mon 9/8

8:40 pm-10:15 pm

Nonstop1h 35m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 9/24

6:35 am-1:25 pm

2 stops6h 50m

Chicago Midway

Sat 9/27

8:15 am-9:50 am

Nonstop1h 35m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 10/28

7:00 am-4:50 pm

2 stops9h 50m

Chicago Midway

Wed 10/29

3:55 pm-5:20 pm

Nonstop1h 25m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 9/6

6:15 am-1:30 pm

2 stops7h 15m

Chicago Midway

Sat 9/13

3:10 pm-4:45 pm

Nonstop1h 35m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 11/11

5:45 am-12:30 pm

2 stops6h 45m

Chicago Midway

Sat 11/22

12:25 pm-1:55 pm

Nonstop1h 30m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 9/4

6:35 am-1:30 pm

2 stops6h 55m

Chicago Midway

Sat 9/6

10:35 am-12:10 pm

Nonstop1h 35m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 18 results
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The best insider tips for Minneapolis to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Minneapolis to Chicago Midway Airport trip
Airports
MSP

Security lines at MSP are generally efficient, but during peak travel periods, waits can approach an hour. Typically, expect less than a half-hour wait.

Read more about MSPby Brandon Schultz
MDW

The Orange Line train is the easiest way to reach downtown Chicago from MDW, taking less than 30 minutes and operating almost 24 hours.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on MSP

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Best time to book a flight from Minneapolis to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Minneapolis 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 Minneapolis to Chicago Midway Airport

How far ahead should I book a flight from Minneapolis to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Minneapolis to Midway. Price data was last updated on August 8, 2025.

Booking 65 days in advance of your planned departure date is, on average, the best time to get cheap flights from Minneapolis to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, April is the cheapest month in which you can book a flight from Minneapolis to Chicago Midway Airport (average of $160). Flying from Minneapolis to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MSP to MDW?

Find hourly flight availability from Minneapolis 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 August 14, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 16% on flights from Minneapolis to Chicago Midway Airport by exploring options for tickets in the evening.

What is the cheapest day to fly from Minneapolis to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Minneapolis to Midway. Price data was last updated on August 10, 2025.

Travelers seeking maximum savings on their Minneapolis to Chicago Midway Airport flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Minneapolis to Chicago Midway Airport

Explore weekly flight availability from Minneapolis to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 14, 2025.

The most flights from MSP to MDW are scheduled on a Wednesday (12 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 on average).

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 August 14, 2025.
Read reviews from past customers who have flown Southwest and Delta from Minneapolis 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
4,244 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Minneapolis 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 Minneapolis to Chicago Midway?

    Minneapolis St Paul (MSP), located 7.3 mi from the city center, is the airport you fly out of when you book flights from Minneapolis to Chicago Midway. 2 airlines have flights from Minneapolis St Paul to Chicago Midway on a regular basis. Booking flights from Minneapolis St Paul to Chicago Midway should not be difficult; the airport handles an average of 9 outbound flights to Chicago Midway per day.

  • What are the cheapest airlines flying from Minneapolis to Chicago Midway Airport round-trip?

    Flying on Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $97. Another option worth looking into is Southwest, starting at $97 round trip. You may be able to fly from Minneapolis to Chicago Midway Airport for 56% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Minneapolis to Chicago Midway Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Minneapolis to Chicago Midway Airport on time: WestJet (86%), Air France (81%), SkyWest Airlines (81%).

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

    On average you can expect to pay $227 for a flight from Minneapolis to Chicago Midway Airport. The cheapest flight overall is $61 while the most popular route, (Minneapolis St Paul - Chicago Midway) is currently priced at $77.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Minneapolis 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 Minneapolis to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Minneapolis to Chicago Midway Airport (average of $160). Flying from Minneapolis to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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Top 2 airlines flying from Minneapolis to Midway

Discover the top 2 airlines that operate flights from Minneapolis 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$97Average$277FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$97Average$223FlexibilityNo cancel feeOn-time63%

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