MKE - CHI

$99 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 6/30. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$188
Overall average: $179
United Airlines
Sat 10/31Tue 11/10
MKE - ORD • Non-stop
Cheapest non-stop
$197
Typical prices: $273-$219
United Airlines
Tue 6/23Tue 6/30
MKE - ORD • Non-stop
Top airlines
Cheapest • from $188 (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 09m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 89% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
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 Chicago!
Flight Deals
Booking Insights
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

Sat, Oct 31 - Tue, Nov 10
United Airlines Logo
10:45 am - 11:45 am
MKE
-
ORD
1h 00mnonstop
United Airlines Logo
4:20 pm - 5:13 pm
ORD
-
MKE
0h 53mnonstop
$188United Airlines
Tue, Jun 23 - Tue, Jun 30
United Airlines Logo
10:38 am - 11:48 am
MKE
-
ORD
1h 10mnonstop
United Airlines Logo
8:45 am - 9:53 am
ORD
-
MKE
1h 08mnonstop
$197United Airlines
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
6:00 am - 6:50 am
MKE
-
MDW
0h 50mnonstop
Southwest Logo
9:10 pm - 10:00 pm
MDW
-
MKE
0h 50mnonstop
$197Southwest
Tue, Jun 23 - Tue, Jun 30
American Airlines Logo
10:00 am - 11:12 am
MKE
-
ORD
1h 12mnonstop
American Airlines Logo
9:20 pm - 10:24 pm
ORD
-
MKE
1h 04mnonstop
$198American Airlines
Tue, Jun 23 - Tue, Jun 30
American Airlines Logo
5:00 am - 6:12 am
MKE
-
ORD
1h 12mnonstop
American Airlines Logo
5:21 pm - 6:20 pm
ORD
-
MKE
0h 59mnonstop
$201American Airlines
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
5:05 pm - 10:35 pm
MKE
-
MDW
5h 30m
1 stop
Southwest Logo
9:10 pm - 10:00 pm
MDW
-
MKE
0h 50mnonstop
$207Southwest
Wed, Jul 22 - Sun, Jul 26
American Airlines Logo
6:01 am - 7:23 am
MKE
-
ORD
1h 22mnonstop
American Airlines Logo
6:59 pm - 8:00 pm
ORD
-
MKE
1h 01mnonstop
$208American Airlines
Wed, Sep 30 - Fri, Oct 2
Southwest Logo
6:40 am - 7:30 am
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:05 pm - 10:50 pm
MDW
-
MKE
0h 45mnonstop
$208Southwest
Sat, Aug 15 - Sat, Aug 15
American Airlines Logo
6:00 am - 7:21 am
MKE
-
ORD
1h 21mnonstop
American Airlines Logo
6:56 pm - 7:59 pm
ORD
-
MKE
1h 03mnonstop
$217American Airlines
Fri, Jul 3 - Mon, Jul 6
United Airlines Logo
5:00 am - 5:59 am
MKE
-
ORD
0h 59mnonstop
United Airlines Logo
5:59 am - 7:00 am
ORD
-
MKE
1h 01mnonstop
$219United 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 cheapest return flight from Milwaukee to Chicago costs $266 on the route between Milwaukee (MKE) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 1% 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 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 November and February, where the average cost of round-trip tickets is $284 and $233 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$99
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 $99 for a one-way ticket and $188 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, American Airlines, 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 $191 or less one-way and $362 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 11644 reviews
7.2Comfort
6.4Food
7.9Crew
6.9Entertainment
7.5Boarding
Airline reviews

The flight from LA to Chicago was smooth and service was very good overall.

8.0 ExcellentAnonymous, Jun 2026
LAX - ORD
Read more American Airlines reviews

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

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.

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

Information on your arrival and departure airports