$39 Cheap Flights from Minneapolis (MSP) to Chicago (MDW)

View $39 flight on Mon, Jun 2, 2025Opens in a new window

Popular airlines from Minneapolis - St. Paul Intl. Airport (MSP) to Chicago Midway Airport (MDW)

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Find available prices by choosing your travel dates.

Cheap Flights from Minneapolis to Chicago (MSP-MDW)

Prices were available within the past 7 days and start at $39 for one-way flights and $77 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Jun 18 - Mon, Jun 23
MSP
Minneapolis
MDW
Chicago
$77 Roundtrip, just found
$77
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Jun 18 from Minneapolis to Chicago, returning Mon, Jun 23, priced at $77 just found
Delta
Tue, Jul 29 - Thu, Aug 7
MSP
Minneapolis
MDW
Chicago
$77 Roundtrip, just found
$77
Roundtrip
just found
Select Delta flight, departing Tue, Jul 29 from Minneapolis to Chicago, returning Thu, Aug 7, priced at $77 just found
Southwest Airlines
Wed, Jun 18 - Mon, Jun 23
MSP
Minneapolis
MDW
Chicago
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Jun 18 from Minneapolis to Chicago, returning Mon, Jun 23, priced at $87 just found
Southwest Airlines
Wed, May 28 - Thu, May 29
MSP
Minneapolis
MDW
Chicago
$92 Roundtrip, just found
$92
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, May 28 from Minneapolis to Chicago, returning Thu, May 29, priced at $92 just found
Southwest Airlines
Mon, Jun 9 - Thu, Jun 12
MSP
Minneapolis
MDW
Chicago
$97 Roundtrip, just found
$97
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Jun 9 from Minneapolis to Chicago, returning Thu, Jun 12, priced at $97 just found
Southwest Airlines
Mon, May 12 - Wed, May 14
MSP
Minneapolis
MDW
Chicago
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, May 12 from Minneapolis to Chicago, returning Wed, May 14, priced at $97 found 2 days ago
Southwest Airlines
Thu, Jul 3 - Mon, Jul 7
MSP
Minneapolis
MDW
Chicago
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Jul 3 from Minneapolis to Chicago, returning Mon, Jul 7, priced at $102 found 3 hours ago
Southwest Airlines
Mon, May 12 - Wed, May 14
MSP
Minneapolis
MDW
Chicago
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, May 12 from Minneapolis to Chicago, returning Wed, May 14, priced at $107 found 2 days ago
Delta
Wed, May 28 - Thu, May 29
MSP
Minneapolis
MDW
Chicago
$107 Roundtrip, just found
$107
Roundtrip
just found
Select Delta flight, departing Wed, May 28 from Minneapolis to Chicago, returning Thu, May 29, priced at $107 just found
Frontier Airlines
Mon, May 19 - Sat, May 24
MSP
Minneapolis
MDW
Chicago
$180 Roundtrip, found 3 hours ago
$180
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, May 19 from Minneapolis to Chicago, returning Sat, May 24, priced at $180 found 3 hours ago

Frequently asked questions

How much does a flight from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW) cost?
You’ll find cheap return flights from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW) starting at $92. Grab your seat and set off on your next adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MSP on May 12 2025 and touching down at MDW. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from MSP to MDW?
The cheapest flights from MSP to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW)?
Take a nonstop flight with Southwest Airlines and travel straight from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from MSP to MDW?
Take off from MSP to MDW with Southwest Airlines. This carrier currently has the cheapest one-way fare on this route, starting from $49. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MSP on June 11 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW)?
With an average of 6 nonstop flights that operate from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW) every day, you’ll be jetting off in no time.
What are the most popular departure times for flights from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW)?
The 11 AM departures from MSP to MDW are the top choice for many travelers. Greater demand means you’ll likely pay more for these departures. If you’re looking to save, choose a less crowded time to fly.
What day of the week has the most flights from MSP to MDW?
If you fly on a Friday, you’ll get the greatest range of choices for flights from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW).
What is the earliest flight from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 5:55AM UTC-6, heading out of Minneapolis - St. Paul Intl. Airport (MSP). You’ll be in the air for roughly 1h 45m, touching down at Midway Intl. Airport (MDW) at approximately 7:40AM UTC-6.
How long does it take to fly from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW)?
Flights from MSP to MDW have an average travel time of 1 hour and 37 minutes. The total distance between these two airports is 350 mi.
What airline has the least delays from MSP to MDW?
With 92% of flights usually arriving on schedule, Southwest Airlines has the best on-time performance for direct flights from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW). To monitor your flight status and get notifications about any changes, simply head to the Expedia App.
What is the best time to fly from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Departures after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Minneapolis - St. Paul Intl. Airport (MSP)?
Take a direct flight from Minneapolis - St. Paul Intl. Airport (MSP) to Chicago and arrive at O’Hare Intl. Airport (ORD). An alternative point of entry into this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from MSP to MDW just before your trip is typically more expensive. However, if there’s some wiggle room with your travel times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a MSP to MDW flight and hotel package?
Securing a MSP to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our wide range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Minneapolis - St. Paul Intl. Airport (MSP) to Midway Intl. Airport (MDW)?
If you reserved your MSP to MDW flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.
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