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$69+ Cheap flights from Wisconsin 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Wisconsin to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Wisconsin (USWI) 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 January 21, 2025.

Round-trip from

$149
(Mytrip)

One-way from

$69
(Southwest)
From Wisconsin to Chicago Midway
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One-way flight from Wisconsin to Chicago Midway
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Find flight deals from Wisconsin to Midway

Cheapest flights from Wisconsin to Midway
Explore the most affordable flight options available from Wisconsin to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2112:53 pmMSP - MDW
1 stop11h 24mFrontier
Tue 2/257:05 amMDW - MSP
1 stop16h 23mFrontier
Deal found 1/20$149
This Southwest deal was found by Cheapflights users on 1/21. 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 3/66:30 amMSP - MDW
1 stop8h 20mSouthwest
Wed 3/126:20 pmMDW - MSP
1 stop4h 30mSouthwest
Deal found 1/21$157
This Delta deal was found by Cheapflights users on 1/21. 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 2/229:00 amMSP - MDW
Nonstop1h 42mDelta
Mon 2/246:59 pmMDW - MSP
Nonstop1h 43mDelta
Deal found 1/21$176
This Delta deal was found by Cheapflights users on 1/20. 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 4/12:34 pmDLH - MDW
1 stop3h 44mDelta
Mon 4/710:25 amMDW - DLH
1 stop3h 29mDelta
Deal found 1/20$198
This Delta deal was found by Cheapflights users on 1/21. 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 2/46:15 amATW - MDW
1 stop6h 27mDelta
Wed 2/52:08 pmMDW - ATW
1 stop6h 21mDelta
Deal found 1/21$209
This Delta deal was found by Cheapflights users on 1/20. 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 2/56:18 amGRB - MDW
1 stop6h 24mDelta
Sun 2/95:05 pmMDW - GRB
1 stop4h 20mDelta
Deal found 1/20$397
This Delta deal was found by Cheapflights users on 1/21. 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.
Fri 2/217:00 amCWA - MDW
1 stop5h 42mDelta
Sun 2/2310:19 amMDW - CWA
1 stop5h 17mDelta
Deal found 1/21$455
This Delta deal was found by Cheapflights users on 1/21. 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.
Mon 3/106:15 amESC - MDW
1 stop3h 30mDelta
Thu 3/1310:25 amMDW - ESC
1 stop3h 39mDelta
Deal found 1/21$517

Find flights from Wisconsin to Midway within your budget

Customize your flight search to find flights from Wisconsin 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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 2/21

12:53 pm-12:17 am

1 stop11h 24m

Chicago Midway

Tue 2/25

7:05 am-11:28 pm

1 stop16h 23m

$149

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 3/1

7:30 am-9:15 am

Nonstop1h 45m

Chicago Midway

Mon 3/3

9:15 pm-10:40 pm

Nonstop1h 25m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 2/22

4:05 pm-5:43 pm

Nonstop1h 38m

Chicago Midway

Mon 2/24

1:26 pm-3:05 pm

Nonstop1h 39m

$176

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 4/1

2:34 pm-6:18 pm

1 stop3h 44m

Chicago Midway

Mon 4/7

10:25 am-1:54 pm

1 stop3h 29m

$198

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Tue 2/4

6:15 am-12:42 pm

1 stop6h 27m

Chicago Midway

Wed 2/5

2:08 pm-8:29 pm

1 stop6h 21m

$209

Green BayChicago

GRB - MDW

GRBMDW

Green Bay Austin-Straubel

Wed 2/5

6:18 am-12:42 pm

1 stop6h 24m

Chicago Midway

Sun 2/9

5:05 pm-9:25 pm

1 stop4h 20m

$397

WausauChicago

CWA - MDW

CWAMDW

Wausau Central Wisconsin

Fri 2/21

7:00 am-12:42 pm

1 stop5h 42m

Chicago Midway

Sun 2/23

10:19 am-3:36 pm

1 stop5h 17m

$455

EscanabaChicago

ESC - MDW

ESCMDW

Escanaba Delta County Arpt

Mon 3/10

6:15 am-8:45 am

1 stop3h 30m

Chicago Midway

Thu 3/13

10:25 am-3:04 pm

1 stop3h 39m

$517

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 2/19

7:47 am-9:35 am

Nonstop1h 48m

$69

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 2/22

10:39 am-7:29 pm

1 stop8h 50m

$75

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 18 results
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Best time to book a flight from Wisconsin to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Wisconsin 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.

Travel insights for flights from Wisconsin to Midway

Get recent, data-driven insights about flights from Wisconsin to Midway including ideal travel times, pricing trends, and more.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 21, 2025.
To help decide which airline to fly from Wisconsin to Chicago, see what other customers have to say about Delta, Frontier and Southwest. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

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

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

    One-way options have recently been found by users for as low as $69 on Southwest. Other airlines that offer cheap prices include Frontier from $75 and Delta from $99 one-way.

  • What are the most popular routes from Wisconsin to Chicago Midway Airport?

    While some choose either Duluth Intl - Chicago Midway or Appleton Intl - Chicago Midway, Minneapolis St Paul - Chicago Midway is the most popular route from Wisconsin to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Wisconsin to Chicago Midway Airport (average of $160). Flying from Wisconsin 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 Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Wisconsin 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 Wisconsin to Midway

Discover the top airline that operate flights from Wisconsin 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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$178Average$238FlexibilityNo cancel feeOn-time69%
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