$86+ Cheap flights from Midway (MDW) to Milwaukee (MKE)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Nov 26 — Dec 31
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Milwaukee with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Milwaukee
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to MilwaukeeExplore the most affordable flight options available from Midway to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2026.
Explore the most affordable flight options available from Midway to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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 11/129:15 pm -
Nonstop1h 00m
Mon 11/166:20 am -
Nonstop1h 00m
Deal found 10/23![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1910:10 am -
Nonstop0h 50m
Mon 11/235:30 am -
Nonstop1h 05m
Deal found 10/26![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 10/23. 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 11/2010:10 am -
Nonstop0h 50m
Fri 11/274:50 pm -
Nonstop0h 50m
Deal found 10/23![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 10/23. 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 12/85:25 pm -
1 stop4h 55m
Tue 12/1511:30 am -
1 stop5h 40m
Deal found 10/23![Southwest logo]()
$191
Best flights from Midway to MilwaukeeDiscover carefully curated flight deals from Midway to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
Discover carefully curated flight deals from Midway to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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 11/129:15 pm -
Nonstop1h 00m
Mon 11/166:20 am -
Nonstop1h 00m
Deal found 10/23![Southwest logo]()
$173
This Southwest deal was found by Cheapflights users on 10/23. 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 12/85:25 pm -
1 stop4h 55m
Tue 12/154:20 pm -
Nonstop0h 55m
Deal found 10/23![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1910:10 am -
Nonstop0h 50m
Mon 11/234:50 pm -
Nonstop0h 50m
Deal found 10/26![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 10/23. 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 11/206:30 am -
1 stop3h 10m
Fri 11/2710:15 am -
1 stop5h 45m
Deal found 10/23![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 10/24. 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 11/1410:15 am -
Nonstop0h 50m
Mon 11/166:20 am -
Nonstop1h 00m
Deal found 10/24![Southwest logo]()
$223
Last-minute flights from Midway to MilwaukeeDiscover last-minute flight deals from Midway to Milwaukee. Data last updated October 27, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Milwaukee. Data last updated October 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/23. 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 11/129:15 pm -
Nonstop1h 00m
Mon 11/166:20 am -
Nonstop1h 00m
Deal found 10/23![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1910:10 am -
Nonstop0h 50m
Mon 11/235:30 am -
Nonstop1h 05m
Deal found 10/26![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 10/23. 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 11/2010:10 am -
Nonstop0h 50m
Fri 11/274:50 pm -
Nonstop0h 50m
Deal found 10/23![Southwest logo]()
$187
One-way flights from Midway to MilwaukeeSearch for one-way flight options from Midway to Milwaukee. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
Search for one-way flight options from Midway to Milwaukee. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 12/710:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$86
This Southwest deal was found by Cheapflights users on 10/23. 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 12/19:10 pm -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$87
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 12/1010:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$93
This Southwest deal was found by Cheapflights users on 10/23. 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 11/209:15 pm -
Nonstop1h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$95
This Southwest deal was found by Cheapflights users on 10/24. 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.
Mon 12/214:20 pm -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 10/24. 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 12/279:30 pm -
Nonstop0h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$135
Find flight deals from Midway to Milwaukee
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Milwaukee (MKE). 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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (Southwest) |
One-way from | $86 (Southwest) |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Milwaukee 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 7,457,451 searches. Data last updated October 27, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Tue 12/1
9:10 pm-10:15 pm
Nonstop1h 05m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$87
Quickest round-trip
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 12/10
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Sun 12/6
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$95
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 11/20
6:30 am-9:40 am
1 stop3h 10m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Mon 12/7
11:45 am-3:15 pm
1 stop3h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$122
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Mon 12/21
4:20 pm-11:10 pm
1 stop6h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$127
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 11/12
9:15 pm-10:15 pm
Nonstop1h 00m
Milwaukee-Mitchell
Mon 11/16
6:20 am-7:20 am
Nonstop1h 00m
$173
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Tue 12/8
5:25 pm-10:20 pm
1 stop4h 55m
Milwaukee-Mitchell
Tue 12/15
4:20 pm-5:15 pm
Nonstop0h 55m
$181
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 11/19
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Mon 11/23
4:50 pm-5:40 pm
Nonstop0h 50m
$185
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 11/20
6:30 am-9:40 am
1 stop3h 10m
Milwaukee-Mitchell
Fri 11/27
10:15 am-4:00 pm
1 stop5h 45m
$209
Showing 1-10 of 11 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Milwaukee 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 Chicago Midway Airport-Milwaukee 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 Midway to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Midway with our price prediction graph.
MDW-MKE
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 Chicago Midway Airport to Milwaukee
Related info for your journey
Find useful and relevant information for your journey from Midway to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsPort Washington
Sheboygan
New Berlin
Oak Creek
Wauwatosa
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