MKE - MDW

$100 Find Cheap Flights from Milwaukee to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Midway departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$218
Southwest
Wed 12/3Thu 12/4
MKE - MDW • 1 stop
Cheapest one-way
$100
Southwest
Wed 12/3
MKE - MDW • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Milwaukee to Midway (MKE-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Midway

Wed, Dec 3 - Thu, Dec 4
Southwest Logo
4:05 pm - 10:35 pmMKE-MDW
6h 30m1 stop
Southwest Logo
6:20 am - 11:40 amMDW-MKE
5h 20m1 stop
$218Southwest
Find Deal
Tue, Dec 2 - Sat, Dec 6
Southwest Logo
8:35 am - 3:25 pmMKE-MDW
6h 50m1 stop
Southwest Logo
1:15 pm - 6:55 pmMDW-MKE
5h 40m1 stop
$264Southwest
Find Deal
Tue, Dec 2 - Sat, Dec 6
Southwest Logo
5:30 am - 9:55 amMKE-MDW
4h 25m1 stop
Southwest Logo
8:25 am - 3:50 pmMDW-MKE
7h 25m2 stops
$269Southwest
Find Deal
Tue, Dec 23 - Tue, Dec 30
Southwest Logo
5:50 am - 10:05 amMKE-MDW
4h 15m1 stop
Southwest Logo
5:45 am - 10:25 amMDW-MKE
4h 40m1 stop
$297Southwest
Find Deal
Tue, Nov 25 - Fri, Nov 28
Southwest Logo
5:50 am - 10:05 amMKE-MDW
4h 15m1 stop
Southwest Logo
5:05 am - 10:20 amMDW-MKE
5h 15m1 stop
$298Southwest
Find Deal
Mon, Nov 24 - Tue, Nov 25
Southwest Logo
5:50 am - 9:55 amMKE-MDW
4h 05m1 stop
Southwest Logo
7:05 pm - 12:30 amMDW-MKE
5h 25m1 stop
$303Southwest
Find Deal
Tue, Dec 23 - Tue, Dec 30
Southwest Logo
5:50 am - 10:05 amMKE-MDW
4h 15m1 stop
Southwest Logo
5:25 pm - 11:45 pmMDW-MKE
6h 20m2 stops
$322Southwest
Find Deal
Tue, Nov 25 - Fri, Nov 28
Southwest Logo
5:50 am - 10:05 amMKE-MDW
4h 15m1 stop
Southwest Logo
9:30 am - 5:25 pmMDW-MKE
7h 55m2 stops
$328Southwest
Find Deal
Fri, Dec 19 - Fri, Dec 26
Southwest Logo
11:25 am - 5:55 pmMKE-MDW
6h 30m1 stop
Southwest Logo
4:20 pm - 10:45 pmMDW-MKE
6h 25m1 stop
$329Southwest
Find Deal
Sat, Dec 20 - Sat, Jan 3
Multiple Airlines Logo
6:00 am - 10:12 pmMKE-MDW
16h 12m2 stops
Multiple Airlines Logo
2:16 pm - 7:21 pmMDW-MKE
29h 05m1 stop
$1,277Multiple Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Milwaukee to Midway flights

Get data-powered insights and trends into flights from Milwaukee to Midway to help you find the cheapest flights, the best time to fly and much more.

How often are flights from Milwaukee to Chicago delayed?

Weekly flights between Milwaukee and Chicago historically see delays in approximately 22% of cases, with the average delay over the past year being 83 minutes.

What is the most punctual flight time for Milwaukee to Chicago flights?

Typically, flights leaving in the morning tend to face fewer delays, whereas flights in the early afternoon have historically encountered delays more often.

What day of the week experiences the fewest flight delays on this route?

Statistically, Tuesday is the day of the week with the fewest delays on this flight route, while Friday has typically experienced more delays than other days.

Which airline has the best punctuality record on Milwaukee to Chicago flights?

Based on our data, Frontier has experienced the fewest delays on this route in the past 12 months, with no flights being classified as delayed.

Find deals

Good to know

Cheapest flight$100
Flight from Milwaukee to Chicago Midway Airport

When to book flights from Milwaukee to Midway

Are your dates flexible? Find out the best times to travel from Milwaukee to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Milwaukee to Chicago Midway Airport flights

  • What is the cheapest flight from Milwaukee to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Milwaukee to Chicago Midway Airport was $100 for a one-way ticket and $218 for a round-trip.

  • Do I need a passport to fly between Milwaukee and Chicago Midway Airport?

    No

  • Which airports will I be using when flying from Milwaukee to Chicago Midway Airport?

    Milwaukee and Chicago Midway Airport are both served by 1 main airport. You will leave Milwaukee from Milwaukee-Mitchell and will be arriving at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Milwaukee to Chicago Midway Airport?

    Only American Airlines offers inflight Wi-Fi service on the Milwaukee to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Milwaukee to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Milwaukee to Chicago Midway Airport flight route.

  • How does KAYAK find such low prices on flights from Milwaukee to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Milwaukee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Milwaukee with another airline. Booking your flights between Milwaukee and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Milwaukee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Milwaukee to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $386 or less round-trip.

Everything you need to know for your flight from Milwaukee to Midway

Information on your arrival and departure airports

Milwaukee (MKE)
Midway (MDW)