MKE - CHI

$89 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 4/18. 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
$181
United Airlines
Mon 3/16Wed 3/18
MKE - ORD • Non-stop
Cheapest one-way
$89
Typical prices: $122-$206
American Airlines
Sat 4/18
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
United Airlines
Cheapest • from $181 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 1h 04m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
MKE
-
ORD
Cheapest • 1% average savings
MKE
-
ORD
Most popular
Insights
Insights
Insights
Insights
Avoid delays
SkyWest Airlines
Most punctual • 89% on-time
Night flights
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

Mon, Mar 16 - Wed, Mar 18
United Airlines Logo
2:54 pm - 4:00 pm
MKE
-
ORD
1h 06mnonstop
United Airlines Logo
11:30 am - 12:35 pm
ORD
-
MKE
1h 05mnonstop
$181United Airlines
Thu, Mar 26 - Sun, Mar 29
United Airlines Logo
6:00 am - 7:03 am
MKE
-
ORD
1h 03mnonstop
United Airlines Logo
8:10 pm - 9:18 pm
ORD
-
MKE
1h 08mnonstop
$190United Airlines
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
4:00 pm - 4:50 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
12:20 pm - 5:15 pm
MDW
-
MKE
4h 55m
1 stop
$191Southwest
Tue, Mar 24 - Tue, Apr 7
United Airlines Logo
11:30 am - 12:36 pm
MKE
-
ORD
1h 06mnonstop
United Airlines Logo
3:45 pm - 4:47 pm
ORD
-
MKE
1h 02mnonstop
$191United Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
9:08 am - 10:20 am
MKE
-
ORD
1h 12mnonstop
American Airlines Logo
2:54 pm - 3:56 pm
ORD
-
MKE
1h 02mnonstop
$192American Airlines
Mon, Mar 16 - Sat, Mar 21
American Airlines Logo
7:52 am - 9:03 am
MKE
-
ORD
1h 11mnonstop
American Airlines Logo
7:16 pm - 8:15 pm
ORD
-
MKE
0h 59mnonstop
$195American Airlines
Sat, Jul 11 - Sat, Aug 1
Southwest Logo
5:45 am - 6:35 am
MKE
-
MDW
0h 50mnonstop
Southwest Logo
8:55 pm - 9:45 pm
MDW
-
MKE
0h 50mnonstop
$197Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
4:00 pm - 4:50 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:10 am - 10:55 am
MDW
-
MKE
0h 45mnonstop
$199Southwest
Mon, Mar 9 - Mon, Mar 16
American Airlines Logo
4:47 pm - 5:49 pm
MKE
-
ORD
1h 02mnonstop
American Airlines Logo
10:10 pm - 11:07 pm
ORD
-
MKE
0h 57mnonstop
$203American Airlines
Fri, Mar 6 - Mon, Mar 9
American Airlines Logo
9:00 am - 10:06 am
MKE
-
ORD
1h 06mnonstop
American Airlines Logo
7:26 pm - 8:25 pm
ORD
-
MKE
0h 59mnonstop
$206American 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 $240 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, 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 Monday. On your return trip to Milwaukee, you should consider flying back on a Monday, and avoid Tuesdays 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$89
Most popular time to fly with an average 9% increase in price.
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 $89 for a one-way ticket and $181 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?

    American Airlines, Delta, and JetBlue 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 $177 or less one-way and $323 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.
7.2
American AirlinesOverall score based on 11334 reviews
8.0Crew
6.9Entertainment
7.2Comfort
7.5Boarding
6.4Food
Airline reviews

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

2.0 MediocreMarius, Feb 2026
LGA - ORD
Read more American Airlines reviews

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

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.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

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$8600h 45m
Trains$421h 34m