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 7/28. 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
Typical prices: $191-$242
American Airlines
Wed 8/5Wed 8/12
MKE - ORD • Non-stop
Cheapest one-way
$86
Typical prices: $194-$331
United Airlines
Tue 7/28
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 10m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 2% average savings
Most popular
Insights
Insights
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Avoid delays
Most punctual • 89% on-time
Best time • Fewest delays
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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

Wed, Aug 5 - Wed, Aug 12
American Airlines Logo
6:01 am - 7:22 am
MKE
-
ORD
1h 21mnonstop
American Airlines Logo
10:05 am - 11:02 am
ORD
-
MKE
0h 57mnonstop
$171American Airlines
Wed, Aug 12 - Wed, Aug 19
Southwest Logo
3:40 pm - 4:30 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:15 am - 11:05 am
MDW
-
MKE
0h 50mnonstop
$171Southwest
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
5:00 am - 6:14 am
MKE
-
ORD
1h 14mnonstop
American Airlines Logo
10:05 am - 11:02 am
ORD
-
MKE
0h 57mnonstop
$172American Airlines
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
1:30 pm - 2:20 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
8:40 pm - 9:25 pm
MDW
-
MKE
0h 45mnonstop
$173Southwest
Mon, Aug 10 - Mon, Aug 17
American Airlines Logo
6:48 pm - 8:21 pm
MKE
-
ORD
1h 33mnonstop
American Airlines Logo
7:58 pm - 9:00 pm
ORD
-
MKE
1h 02mnonstop
$175American Airlines
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
5:45 am - 6:30 am
MKE
-
MDW
0h 45mnonstop
Southwest Logo
8:40 pm - 9:25 pm
MDW
-
MKE
0h 45mnonstop
$175Southwest
Sat, Aug 8 - Mon, Aug 10
United Airlines Logo
8:50 am - 10:00 am
MKE
-
ORD
1h 10mnonstop
United Airlines Logo
7:45 pm - 8:56 pm
ORD
-
MKE
1h 11mnonstop
$181United Airlines
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
1:30 pm - 2:20 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
8:40 pm - 9:25 pm
MDW
-
MKE
0h 45mnonstop
$181Southwest
Sat, Aug 8 - Mon, Aug 10
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
$182American Airlines
Mon, Nov 23 - Fri, Nov 27
United Airlines Logo
6:18 pm - 7:30 pm
MKE
-
ORD
1h 12mnonstop
United Airlines Logo
5:45 pm - 6:48 pm
ORD
-
MKE
1h 03mnonstop
$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 absolute cheapest return flight from Milwaukee to Chicago costs $259 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, 2% 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$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 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Milwaukee and Chicago, with oneworld 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 $184 or less one-way and $372 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 11768 reviews
6.4Food
7.2Comfort
7.5Boarding
7.9Crew
6.8Entertainment
Airline reviews

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

6.0 GoodDanielle, Jun 2026
BHM - ORD
Read more American Airlines reviews

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

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$1,5380h 45m
Trains$451h 34m
Buses$411h 45m