MKE - CHI

$86 Find Cheap Flights from Milwaukee to Chicago - Compare and Save

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 Chicago departing on 1/23. 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

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Everything you should know

Cheapest round-trip
$171
Southwest
Mon 8/24Sat 8/29
MKE - MDW • Non-stop
Cheapest non-stop
$171
Typical prices: $185-$293
United Airlines
Wed 8/26Thu 9/3
MKE - ORD • Non-stop
Top airlines
Cheapest • from $171 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 1h 07m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
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Avoid delays
Most punctual • 88% on-time
Best time • Fewest delays
Insights
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Expert advice
Flight Deals

Cheap Flights from Milwaukee to Chicago (MKE-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Chicago 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 Chicago

Mon, Aug 24 - Sat, Aug 29
Southwest Logo
5:45 am - 6:30 am
MKE
-
MDW
0h 45mnonstop
Southwest Logo
6:10 pm - 7:00 pm
MDW
-
MKE
0h 50mnonstop
$171Southwest
Wed, Aug 26 - Thu, Sep 3
United Airlines Logo
10:19 am - 11:30 am
MKE
-
ORD
1h 11mnonstop
United Airlines Logo
1:30 pm - 2:33 pm
ORD
-
MKE
1h 03mnonstop
$171United Airlines
Tue, Dec 15 - Tue, Jan 12
American Airlines Logo
7:45 am - 9:05 am
MKE
-
ORD
1h 20mnonstop
American Airlines Logo
1:20 pm - 2:24 pm
ORD
-
MKE
1h 04mnonstop
$171American Airlines
Mon, Aug 24 - Sat, Aug 29
United Airlines Logo
1:19 pm - 2:30 pm
MKE
-
ORD
1h 11mnonstop
United Airlines Logo
2:40 pm - 3:47 pm
ORD
-
MKE
1h 07mnonstop
$171United Airlines
Tue, Dec 15 - Tue, Jan 12
United Airlines Logo
12:14 pm - 1:15 pm
MKE
-
ORD
1h 01mnonstop
United Airlines Logo
8:56 am - 9:49 am
ORD
-
MKE
0h 53mnonstop
$171United Airlines
Mon, Aug 24 - Mon, Aug 31
American Airlines Logo
8:20 am - 9:41 am
MKE
-
ORD
1h 21mnonstop
American Airlines Logo
5:27 pm - 6:30 pm
ORD
-
MKE
1h 03mnonstop
$179American Airlines
Thu, Aug 20 - Thu, Aug 27
American Airlines Logo
5:00 am - 6:14 am
MKE
-
ORD
1h 14mnonstop
American Airlines Logo
7:58 pm - 9:00 pm
ORD
-
MKE
1h 02mnonstop
$179American Airlines
Sat, Aug 22 - Mon, Aug 24
Southwest Logo
1:30 pm - 2:20 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:10 am - 11:00 am
MDW
-
MKE
0h 50mnonstop
$179Southwest
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
1:30 pm - 2:20 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
6:10 pm - 7:00 pm
MDW
-
MKE
0h 50mnonstop
$179Southwest
Sat, Sep 19 - Sat, Sep 19
Southwest Logo
5:45 am - 6:30 am
MKE
-
MDW
0h 45mnonstop
Southwest Logo
10:15 am - 11:05 am
MDW
-
MKE
0h 50mnonstop
$179Southwest
Booking Insights

KAYAK's insights & trends for Milwaukee to Chicago flights

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

What is the cheapest Milwaukee to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Milwaukee to Chicago costs $262 on the route between Milwaukee (MKE) and Chicago Midway Airport (MDW). The most popular route is between Milwaukee (MKE) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Milwaukee to Chicago?

The average price of all round-trip flights from Milwaukee to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Sunday. On your return trip to Milwaukee, you should consider flying back on a Friday, and avoid Tuesdays for better deals.

What is the cheapest month to fly from Milwaukee to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to Chicago is July, where tickets cost $0 (return) on average. On the other hand, the most expensive months are October and September, where the average cost of round-trip tickets is $387 and $343 respectively.

Expert advice

Expert advice for your flight from Milwaukee to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Good to know

Cheapest flight

$86
Flight from Milwaukee to Chicago O'Hare Airport

When to book flights from Milwaukee to Chicago

Are your dates flexible? Find out the best times to travel from Milwaukee to Chicago 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 flights from Milwaukee to Chicago

  • What is the cheapest flight from Milwaukee to Chicago?

    In the last 5 days, the lowest price for a flight from Milwaukee to Chicago was $86 for a one-way ticket and $171 for a round-trip.

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

    A passport is not required to fly from Milwaukee to Chicago.

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

    When flying out of Milwaukee you will be using Milwaukee-Mitchell. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

    Delta, JetBlue, and American Airlines offer inflight Wi-Fi service on the Milwaukee to Chicago flight route.

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

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Milwaukee to Chicago flight route.

  • Which airline alliances offer flights from Milwaukee to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between Milwaukee and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Milwaukee to Chicago?

    There are nonstop flights from Milwaukee to Chicago on a daily basis.

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to Milwaukee with another airline.

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

    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 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

  • Looking for a cheap flight? 25% of our users found flights on this route for $205 or less one-way and $356 or less round-trip.

Prefer to fly direct from Milwaukee to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Milwaukee-Mitchell to Chicago.
Find which airlines fly direct from Milwaukee-Mitchell Airport to Chicago, which days they fly and book direct flights.

Direct departures

Milwaukee-Mitchell to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Milwaukee-Mitchell

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top airline flying from Milwaukee to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milwaukee to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11839 reviews
7.5Boarding
7.2Comfort
7.9Crew
6.8Entertainment
6.4Food
Airline reviews

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

10.0 ExcellentAnonymous, Jul 2026
LAX - ORD
Read more American Airlines reviews

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

We were told we had no flights before our flight was continually delayed then cancelled.

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

Information on your arrival and departure airports

Compare transportation modes for Milwaukee to Chicago

Transportation modeAverage priceAverage duration
Flights$1,0650h 45m
Trains$461h 34m
Buses$482h 00m