Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

MKE - CHI

Find cheap flights from Milwaukee to Chicago from $118

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 7/18. 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
0 bags
Mon 6/10
Mon 6/17

Search 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
In the last 7 days travelers have searched 43,156,178 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:21 pm - 7:06 pmMKE-ORD
24h 45m1 stop
6:25 am - 8:09 pmORD-MKE
13h 44m1 stop
$205Sun Country Air
Find Deal
Sun, Jun 9 - Sun, Jun 16
11:31 am - 12:33 pmMKE-ORD
1h 02mnonstop
6:24 pm - 7:21 pmORD-MKE
0h 57mnonstop
$249American Airlines
Find Deal
Tue, Jun 11 - Wed, Jun 12
8:09 am - 9:10 amMKE-ORD
1h 01mnonstop
5:20 pm - 6:07 pmORD-MKE
0h 47mnonstop
$254American Airlines
Find Deal
Sat, Jun 1 - Sat, Jun 8
5:00 am - 8:41 pmMKE-ORD
15h 41m1 stop
8:26 pm - 6:11 pmORD-MKE
21h 45m2 stops
$259Spirit Airlines
Find Deal
Thu, Jun 6 - Mon, Jun 10
5:00 am - 8:41 pmMKE-ORD
15h 41m1 stop
7:22 pm - 6:11 pmORD-MKE
22h 49m3 stops
$262Spirit Airlines
Find Deal
Thu, Jun 6 - Mon, Jun 10
5:00 am - 12:55 amMKE-ORD
19h 55m3 stops
8:26 pm - 6:11 pmORD-MKE
21h 45m2 stops
$275Spirit Airlines
Find Deal
Thu, Jun 6 - Mon, Jun 10
9:07 pm - 6:24 amMKE-ORD
9h 17m1 stop
9:37 pm - 5:16 pmORD-MKE
19h 39m2 stops
Sun, Jun 9 - Sun, Jun 16
9:07 pm - 7:06 pmMKE-ORD
21h 59m2 stops
9:37 pm - 5:16 pmORD-MKE
19h 39m2 stops
Sun, Jun 9 - Sun, Jun 16
5:21 pm - 6:25 pmMKE-ORD
1h 04mnonstop
5:04 am - 9:28 pmORD-MKE
16h 24m1 stop
$386United Airlines
Find Deal
Sat, Jun 1 - Sat, Jun 8
3:51 pm - 4:55 pmMKE-ORD
1h 04mnonstop
9:08 pm - 1:36 pmORD-MKE
16h 28m1 stop
$407United Airlines
Find Deal
Thu, Aug 15 - Tue, Aug 20

Flights from Milwaukee to Chicago - Travel Insights & Trends

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Milwaukee to Chicago.
Our data shows that the cheapest route for a one-way flight from Milwaukee to Chicago cost $129 and was between Milwaukee and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $257.

What’s the cheapest day of the week to fly from Milwaukee to Chicago?

The average price of all flights from Milwaukee to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Milwaukee to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Mondays for the best deals.

Which airlines provide the cheapest flights from Milwaukee to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Milwaukee to Chicago were found on Sun Country Air ($205) and American Airlines ($249). Sun Country Air proposed the cheapest one-way flight at $118.

Which airlines fly non-stop between Milwaukee and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Milwaukee to Chicago.
There are 2 airlines that fly nonstop from Milwaukee to Chicago. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best one-way deal found costing $114. On average, the best prices for this route can be found at United Airlines.

How many flights are there between Milwaukee and Chicago per day?

Each day, there are between 14 and 17 nonstop flights that take off from Milwaukee and land in Chicago, with an average flight time of 1h 03m. The most common departure time is 5:00 am and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 107 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Milwaukee and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Milwaukee to Chicago take?

A direct flight to Chicago will take on average 1h 01m to travel the 75 miles flying distance from Milwaukee.

What’s the earliest departure time from Milwaukee to Chicago?

Early birds can take the earliest flight from Milwaukee at 5:02 am and will be landing in Chicago at 6:03 am.

What’s the latest departure time from Milwaukee to Chicago?

If you prefer to fly at night, the latest flight from Milwaukee to Chicago jets off at 5:30 pm and lands at 6:35 pm.

Good to know

Low season

September

High season

January

Cheapest flight

$118
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly and prices are also 26% lower on average.
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 $118 for a one-way ticket and $205 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, JetBlue, Delta, Alaska Airlines, and Iberia 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 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 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.

  • Which is the best airline for flights from Milwaukee to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Milwaukee to Chicago are United Airlines and American Airlines. With an average price for the route of $169 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $189 and an overall rating of 7.3.

  • 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.

See more FAQs

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 $192 or less one-way and $370 or less round-trip.

Prefer to fly non-stop from Milwaukee to Chicago?

Find which airlines fly direct from Milwaukee-Mitchell to Chicago, which days they fly and book direct flights.

Nonstop departures

Milwaukee-Mitchell to Chicago

Monday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Tuesday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Wednesday

ANA, Aer Lingus, Air Canada, +11 more

ANA, Aer Lingus, +12 more

Thursday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Friday

ANA, Aer Lingus, Air Canada, +11 more

ANA, Aer Lingus, +12 more

Saturday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Sunday

ANA, Aer Lingus, Air Canada, +11 more

ANA, Aer Lingus, +12 more

See more direct flights

Nonstop returns

Chicago to Milwaukee-Mitchell

Monday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Tuesday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Wednesday

ANA, Aer Lingus, Air Canada, +11 more

ANA, Aer Lingus, +12 more

Thursday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Friday

ANA, Aer Lingus, Air Canada, +11 more

ANA, Aer Lingus, +12 more

Saturday

ANA, Aer Lingus, Air Canada, +10 more

ANA, Aer Lingus, +11 more

Sunday

ANA, Aer Lingus, Air Canada, +11 more

ANA, Aer Lingus, +12 more

See more direct flights
See more direct flights

Top airlines 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.
7.4
United AirlinesOverall score based on 11014 reviews
6.7Food
8.1Crew
7.7Boarding
7.2Comfort
7.1Entertainment
Airline reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

8.0 ExcellentMichelle, Apr 2024MBS - ORD
Read more about United Airlines reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

All good except paid for wifi that did not work

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Milwaukee to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Milwaukee to Chicago found on KAYAK in the last 72 hours.
7/18Thu
1 stopSun Country Air
17h 01mMKE-ORD
$118
7/18Thu
nonstopAmerican Airlines
1h 01mMKE-ORD
$140
6/7Fri
1 stopSpirit Airlines
8h 45mMKE-ORD
$156
8/8Thu
1 stopSpirit Airlines
8h 29mMKE-ORD
$190
7/18Thu
2 stops
12h 03mMKE-ORD
$213
7/18Thu
3 stopsSpirit Airlines
25h 01mMKE-ORD
$228
5/16Thu
nonstopUnited Airlines
1h 05mMKE-ORD
$248
6/7Fri
2 stops
13h 54mMKE-MDW
$262
5/16Thu
1 stopSouthwest
8h 00mMKE-MDW
$466
5/16Thu
2 stopsSouthwest
11h 50mMKE-MDW
$512

Search by stops

Search by airline

Search by price

Last minute flights from Milwaukee to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Milwaukee to Chicago that are departing in the next 10 days.
5/16Thu
multi-stopSpirit Airlines
9h 53mMKE-ORD
5/21Tue
multi-stopSpirit Airlines
26h 36mORD-MKE
$386
5/16Thu
multi-stopSpirit Airlines
8h 25mMKE-ORD
5/21Tue
multi-stopSpirit Airlines
6h 15mORD-MKE
$411
5/15Wed
multi-stopSpirit Airlines
14h 06mMKE-ORD
5/18Sat
multi-stopSpirit Airlines
13h 26mORD-MKE
$416
5/15Wed
multi-stopSpirit Airlines
14h 06mMKE-ORD
5/18Sat
multi-stopSpirit Airlines
16h 21mORD-MKE
$439
5/16Thu
multi-stopSpirit Airlines
21h 56mMKE-ORD
5/21Tue
multi-stopSpirit Airlines
26h 36mORD-MKE
$440
5/15Wed
multi-stop
27h 40mMKE-ORD
5/18Sat
multi-stop
22h 50mORD-MKE
$481
5/13Mon
multi-stop
15h 57mMKE-ORD
5/16Thu
multi-stop
24h 56mORD-MKE
$504
5/15Wed
nonstopUnited Airlines
1h 05mMKE-ORD
5/18Sat
nonstopUnited Airlines
0h 58mORD-MKE
$544
5/15Wed
nonstopAmerican Airlines
1h 01mMKE-ORD
5/18Sat
multi-stopAmerican Airlines
5h 35mORD-MKE
$552
5/13Mon
nonstopAmerican Airlines
1h 01mMKE-ORD
5/16Thu
nonstopAmerican Airlines
0h 46mORD-MKE
$579

Search by stops

Search by airline

Search by price

Milwaukee - Chicago Flights

Departure:

Milwaukee (undefined)United States

Return flight deals:

Chicago - Milwaukee

Cabin classes:

$691
$993
$1,120
$257

Compare transportation modes for Milwaukee to Chicago

Average priceAverage duration
Flights$1,6331h 01m
Trains$391h 26m
Buses$761h 53m