MKE - CHI

$72 Find Cheap Flights from Milwaukee to Chicago

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 5/20. 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

 
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
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Everything you should know

Cheapest round-trip
$143
Typical prices: $591-$187
United Airlines
Wed 5/20Wed 5/27
MKE - ORD • Non-stop
Cheapest one-way
$72
Typical prices: $109-$129
American Airlines
Wed 5/20
MKE - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Main Cabin Extra includes early boarding.
United's Economy Plus offers extra legroom for comfort.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $143 (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 11m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 6% average savings
Most popular
Insights
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Avoid delays
Most punctual • 89% on-time
Best time • Fewest delays
Insights
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We hope you love your trip to Chicago!
Flight Deals
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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

Wed, May 20 - Wed, May 27
United Airlines Logo
12:06 pm - 1:15 pm
MKE
-
ORD
1h 09mnonstop
United Airlines Logo
10:11 am - 11:19 am
ORD
-
MKE
1h 08mnonstop
$143United Airlines
Wed, May 20 - Wed, May 27
Southwest Logo
4:05 pm - 4:55 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:10 am - 10:55 am
MDW
-
MKE
0h 45mnonstop
$143Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
4:05 pm - 4:55 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:10 am - 10:55 am
MDW
-
MKE
0h 45mnonstop
$144Southwest
Wed, May 20 - Wed, May 27
Southwest Logo
4:05 pm - 4:55 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
12:20 pm - 5:15 pm
MDW
-
MKE
4h 55m
1 stop
$159Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
8:00 am - 2:55 pm
MKE
-
MDW
6h 55m
1 stop
Southwest Logo
10:10 am - 10:55 am
MDW
-
MKE
0h 45mnonstop
$164Southwest
Mon, May 11 - Mon, May 11
American Airlines Logo
5:06 am - 6:25 am
MKE
-
ORD
1h 19mnonstop
American Airlines Logo
12:22 pm - 1:23 pm
ORD
-
MKE
1h 01mnonstop
$171American Airlines
Wed, May 13 - Wed, May 20
American Airlines Logo
7:01 am - 8:20 am
MKE
-
ORD
1h 19mnonstop
American Airlines Logo
9:40 am - 10:43 am
ORD
-
MKE
1h 03mnonstop
$181American Airlines
Fri, May 15 - Mon, May 18
American Airlines Logo
8:11 am - 9:25 am
MKE
-
ORD
1h 14mnonstop
American Airlines Logo
2:54 pm - 3:56 pm
ORD
-
MKE
1h 02mnonstop
$185American Airlines
Fri, May 22 - Mon, May 25
United Airlines Logo
5:29 pm - 6:40 pm
MKE
-
ORD
1h 11mnonstop
United Airlines Logo
2:40 pm - 3:46 pm
ORD
-
MKE
1h 06mnonstop
$195United Airlines
Thu, May 14 - Thu, May 21
American Airlines Logo
11:13 am - 12:25 pm
MKE
-
ORD
1h 12mnonstop
American Airlines Logo
12:14 pm - 1:13 pm
ORD
-
MKE
0h 59mnonstop
$201American Airlines
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 absolute cheapest return flight from Milwaukee to Chicago costs $256 on the route between Milwaukee (MKE) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Milwaukee (MKE) and Chicago Midway Airport (MDW) were, on average, 6% cheaper than other Milwaukee-Chicago routes. 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 Monday, and avoid Wednesdays for better deals.

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$72
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 3 days, the lowest price for a flight from Milwaukee to Chicago was $72 for a one-way ticket and $143 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, American Airlines, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Milwaukee to Chicago flight route.

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

    The Boeing 737 MAX 8 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 $219 or less one-way and $354 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 11659 reviews
7.9Crew
7.2Comfort
6.4Food
7.5Boarding
6.9Entertainment
Airline reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

10.0 ExcellentDeepa, Apr 2026
DFW - ORD
Read more American Airlines reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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$7130h 50m
Trains$461h 35m