MKE - CHI

$76 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 1/21. 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

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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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

Sun, Nov 16 - Sun, Nov 23
American Airlines Logo
9:05 am - 10:17 amMKE-ORD
1h 12mnonstop
American Airlines Logo
1:55 pm - 2:54 pmORD-MKE
0h 59mnonstop
$179American Airlines
Find Deal
Tue, Nov 4 - Sat, Nov 8
American Airlines Logo
5:00 am - 6:10 amMKE-ORD
1h 10mnonstop
American Airlines Logo
5:34 pm - 6:27 pmORD-MKE
0h 53mnonstop
$189American Airlines
Find Deal
Tue, Nov 18 - Tue, Nov 18
Southwest Logo
9:05 am - 12:40 pmMKE-MDW
3h 35m1 stop
Southwest Logo
5:15 pm - 9:30 pmMDW-MKE
4h 15m1 stop
$219Southwest
Find Deal
Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
7:00 am - 8:11 amMKE-ORD
1h 11mnonstop
United Airlines Logo
2:05 pm - 3:07 pmORD-MKE
1h 02mnonstop
$239United Airlines
Find Deal
Sun, Nov 16 - Sun, Nov 23
Southwest Logo
5:50 am - 9:55 amMKE-MDW
4h 05m1 stop
Southwest Logo
7:00 pm - 11:30 pmMDW-MKE
4h 30m1 stop
$248Southwest
Find Deal
Thu, Apr 16 - Sun, Apr 19
United Airlines Logo
8:29 am - 9:30 amMKE-ORD
1h 01mnonstop
United Airlines Logo
7:51 pm - 8:45 pmORD-MKE
0h 54mnonstop
$273United Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
Multiple Airlines Logo
7:02 pm - 9:48 pmMKE-ORD
26h 46m1 stop
Multiple Airlines Logo
6:48 am - 6:08 pmORD-MKE
11h 20m1 stop
$347Multiple Airlines
Find Deal
Thu, Dec 18 - Mon, Dec 29
Multiple Airlines Logo
6:27 pm - 6:38 pmMKE-ORD
24h 11m1 stop
Multiple Airlines Logo
1:32 pm - 10:15 pmORD-MKE
8h 43m1 stop
$357Multiple Airlines
Find Deal
Fri, Feb 6 - Thu, Feb 12
Spirit Airlines Logo
1:56 pm - 9:23 pmMKE-ORD
7h 27m1 stop
Spirit Airlines Logo
5:05 am - 7:29 pmORD-MKE
14h 24m1 stop
$370Spirit Airlines
Find Deal
Fri, Feb 6 - Thu, Feb 12
Spirit Airlines Logo
12:54 pm - 9:44 amMKE-ORD
20h 50m2 stops
Spirit Airlines Logo
7:56 pm - 11:29 amORD-MKE
15h 33m2 stops
$419Spirit Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
American Airlines
Cheapest • from $179 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MKE-ORD
Cheapest • 27% average savings
MKE-ORD
Most popular
Insights
Insights
Insights
Insights
Cheapest round-trip
$179
Typical prices: $310-$363
American Airlines
Sun 11/16Sun 11/23
MKE - ORD • Non-stop
Cheapest one-way
$76
Southwest
Wed 1/21
MKE - MDW • 1 stop
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We hope you love your trip to Chicago!
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.

How much is a round-trip flight from Milwaukee to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Milwaukee to Chicago departing in November.

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 $226 on the route between Milwaukee (MKE) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 27% cheaper than other Milwaukee-Chicago routes. It is also the most popular route.

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 Friday, and avoid Thursdays for better deals.

Find deals
Expert advice

Expert advice for your flight from Milwaukee to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United offers Priority Boarding to avoid gate-checking your carry-on, ideal for quick flights.


United's Economy Plus seats provide up to six inches more legroom, enhancing comfort on short flights.

Read more about United Airlinesby Stefanie Waldek
American Airlines

American's Main Cabin Extra offers early boarding and complimentary drinks, enhancing short-haul comfort.


American Airlines' Basic Economy is budget-friendly for carry-on travelers with flexible plans.

Read more about American Airlinesby Harriet Baskas
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more

Good to know

Low seasonJune
Cheapest flight$76
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Milwaukee to Chicago Midway 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 $76 for a one-way ticket and $179 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, Alaska Airlines, 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 737-800 Passenger/BBJ2 (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 $166 or less one-way and $319 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, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to Milwaukee-Mitchell

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

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 11029 reviews
7.5Boarding
8.0Crew
6.4Food
7.2Comfort
6.9Entertainment
Airline reviews

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

8.0 ExcellentRachel, Oct 2025CLE - ORD
Read more American Airlines reviews

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

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

Information on your arrival and departure airports

Milwaukee (MKE)

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