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Midway

$72+ Cheap flights from Saint Paul, MN 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — MDW
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheapflights Tip: The best prices from Saint Paul to Chicago Midway are usually found in October or August, booked 65 days in advance, depart on a Thursday or Wednesday and return on a Friday

Cheap flight deals from Saint Paul to Midway

Cheapest flights from Saint Paul to Midway
Explore the most affordable flight options available from Saint Paul to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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 3/114:20 pm
MSP
-
MDW
1 stop6h 30m
Southwest
Wed 3/185:30 pm
MDW
-
MSP
1 stop6h 00m
Southwest
Deal found 1/27$117
This Southwest deal was found by Cheapflights users on 1/27. 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 2/242:30 pm
MSP
-
MDW
1 stop5h 25m
Southwest
Tue 3/31:50 pm
MDW
-
MSP
1 stop8h 00m
Southwest
Deal found 1/27$122
This Southwest deal was found by Cheapflights users on 1/27. 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 3/37:20 am
MSP
-
MDW
Nonstop1h 55m
Southwest
Thu 3/52:20 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 1/27$134
This Southwest deal was found by Cheapflights users on 1/27. 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 4/157:10 am
MSP
-
MDW
2 stops8h 35m
Southwest
Thu 4/169:30 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 1/27$149
This Southwest deal was found by Cheapflights users on 1/27. 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 3/32:30 pm
MSP
-
MDW
1 stop5h 25m
Southwest
Mon 3/95:40 pm
MDW
-
MSP
1 stop5h 45m
Southwest
Deal found 1/27$154
This Southwest deal was found by Cheapflights users on 1/26. 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 4/154:30 pm
MSP
-
MDW
1 stop5h 20m
Southwest
Sat 4/183:30 pm
MDW
-
MSP
2 stops7h 05m
Southwest
Deal found 1/26$159
This Delta deal was found by Cheapflights users on 1/28. 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 3/47:05 am
MSP
-
MDW
Nonstop2h 01m
Delta
Sat 3/79:34 am
MDW
-
MSP
1 stop4h 15m
Delta
Deal found 1/28$167
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/199:58 am
MSP
-
MDW
1 stop11h 14m
Frontier
Thu 2/263:00 pm
MDW
-
MSP
1 stop28h 25m
Frontier
Deal found 1/26$170
This Delta deal was found by Cheapflights users on 1/26. 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 2/194:59 pm
MSP
-
MDW
Nonstop1h 41m
Delta
Mon 2/237:20 pm
MDW
-
MSP
Nonstop1h 40m
Delta
Deal found 1/26$171
This Southwest deal was found by Cheapflights users on 1/26. 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 2/187:20 am
MSP
-
MDW
Nonstop1h 55m
Southwest
Wed 2/251:25 pm
MDW
-
MSP
2 stops7h 10m
Southwest
Deal found 1/26$172

Find flight deals from Saint Paul to Midway

Keep the following information in mind while searching for Saint Paul to Midway flight deals. Data was last updated January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Southwest)

One-way from

$72
(Southwest)

Popular in

January

Cheapest in

October

Average price

$298
Provider with most accurate pricing for Minneapolis St Paul-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Minneapolis St Paul-Chicago (CHI) flights.
Search Deals
From Saint Paul to Chicago Midway
Search Deals
One-way flight from Saint Paul to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Saint Paul 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 January 28, 2026.
Use the filters below to find and compare flights from Saint Paul to Chicago Midway Airport that are best for you.

Fly from

Saint Paul

Fly to

Midway

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 3/3

6:50 am-1:25 pm

1 stop6h 35m

Chicago Midway

Thu 3/5

6:25 pm-12:40 am

1 stop6h 15m

$154

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 2/16

11:20 am-1:05 pm

Nonstop1h 45m

Chicago Midway

Thu 2/26

9:50 am-11:32 am

Nonstop1h 42m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 2/26

4:59 pm-6:40 pm

Nonstop1h 41m

Chicago Midway

Mon 3/2

7:20 pm-9:00 pm

Nonstop1h 40m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 2/16

4:59 pm-6:40 pm

Nonstop1h 41m

Chicago Midway

Wed 2/25

9:50 am-11:32 am

Nonstop1h 42m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 4/16

4:57 pm-6:36 pm

Nonstop1h 39m

Chicago Midway

Sat 4/18

9:46 am-11:27 am

Nonstop1h 41m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 3/11

11:49 am-1:25 pm

Nonstop1h 36m

Chicago Midway

Wed 3/18

9:30 am-11:07 am

Nonstop1h 37m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 2/19

4:59 pm-6:40 pm

Nonstop1h 41m

Chicago Midway

Sat 2/28

5:00 pm-6:52 pm

Nonstop1h 52m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 3/7

2:30 pm-4:14 pm

Nonstop1h 44m

Chicago Midway

Mon 3/9

7:20 pm-9:00 pm

Nonstop1h 40m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 2/21

2:30 pm-4:14 pm

Nonstop1h 44m

Chicago Midway

Tue 2/24

9:50 am-11:32 am

Nonstop1h 42m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 4/7

10:05 am-11:35 am

Nonstop1h 30m

Chicago Midway

Tue 4/14

4:50 pm-11:05 pm

1 stop6h 15m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 22 results
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Best time to book a flight from Saint Paul to Midway

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

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

Use this chart to determine the optimal time to book a round-trip flight from Saint Paul to Midway. Price data was last updated on January 23, 2026.

To ensure you get the cheapest price possible for a flight from Saint Paul to Chicago Midway Airport, you should look to book at least 65 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Saint Paul to Chicago Midway Airport (average of $77). Flying from Saint Paul to Chicago Midway Airport in July is currently the most expensive (average of $191). 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 SA1 to MDW?

Find hourly flight availability from Saint Paul 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 January 28, 2026.

One of the essential ways to save on airfare from Saint Paul to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 9% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Saint Paul to Midway. Price data was last updated on January 24, 2026.

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

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 January 28, 2026.
Read through reviews of airlines operating flights from Saint Paul to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,123 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

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

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

    Departing from Saint Paul to Chicago Midway Airport will take you 1h 45m. Airlines will cover a distance of 348 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Saint Paul to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $48. Delta flights start at $68 while deals on Frontier start at $89 one-way.

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

    The top 3 most reliable airlines when flying from Saint Paul to Chicago Midway Airport are WestJet (76%), Southwest (76%) and SkyWest Airlines (72%).

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

    The cheapest flight price from Saint Paul to Chicago Midway Airport is $120. On average you can expect to pay $308. The most popular route, (Minneapolis St Paul - Chicago Midway), can usually be booked for $97.

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

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

  • How can I find direct flights from Saint Paul to Midway?

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Saint Paul to Chicago Midway Airport (average of $77). Flying from Saint Paul to Chicago Midway Airport in July is currently the most expensive (average of $191). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Saint Paul to Midway

Discover the top 2 airlines that operate flights from Saint Paul 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$97Average$265FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$101Average$219FlexibilityNo cancel feeOn-time63%

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