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$68+ Cheap flights from Chicago (CHI) to Milwaukee (MKE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Chicago to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$143
(Southwest)

One-way from

$68
(Southwest)

Popular in

December

Cheapest in

September

Average price

$183

Good one-way deal

$279 or less
From Chicago (CHI) to Milwaukee-Mitchell
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One-way flight from Chicago (CHI) to Milwaukee-Mitchell
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Highest demand for flights based on searches. 25% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Chicago (CHI) to Milwaukee-Mitchell.
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Find flight deals from Chicago to Milwaukee

Cheapest flights from Chicago to Milwaukee
Explore the most affordable flight options available from Chicago to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/85:50 pmORD - MKE
Nonstop1h 06mUnited Airlines
Wed 10/1510:50 amMKE - ORD
Nonstop1h 10mUnited Airlines
Deal found 9/10$179
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:25 pmORD - MKE
Nonstop1h 00mAmerican Airlines
Sun 11/23:36 pmMKE - ORD
Nonstop1h 12mAmerican Airlines
Deal found 9/11$180
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:04 amORD - MKE
Nonstop1h 00mAmerican Airlines
Mon 9/296:23 pmMKE - ORD
Nonstop1h 16mAmerican Airlines
Deal found 9/10$189
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/169:04 amORD - MKE
Nonstop1h 00mAmerican Airlines
Tue 9/236:19 amMKE - ORD
Nonstop1h 06mAmerican Airlines
Deal found 9/8$199
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/199:04 amORD - MKE
Nonstop1h 00mAmerican Airlines
Sun 9/215:05 amMKE - ORD
Nonstop1h 02mAmerican Airlines
Deal found 9/9$209
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2512:59 pmORD - MKE
Nonstop0h 59mUnited Airlines
Sun 11/306:05 amMKE - ORD
Nonstop1h 11mUnited Airlines
Deal found 9/8$239
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:56 pmORD - MKE
Nonstop1h 04mAmerican Airlines
Tue 9/168:43 amMKE - ORD
Nonstop1h 05mAmerican Airlines
Deal found 9/8$240
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/109:04 amORD - MKE
Nonstop1h 00mAmerican Airlines
Sat 9/136:18 amMKE - ORD
Nonstop1h 06mAmerican Airlines
Deal found 9/8$272
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:24 pmMDW - MKE
1 stop24h 54mMultiple Airlines
Sun 11/21:55 pmMKE - MDW
1 stop18h 37mMultiple Airlines
Deal found 9/11$278
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1312:33 pmORD - MKE
Nonstop0h 47mAmerican Airlines
Mon 9/1510:34 amMKE - ORD
Nonstop1h 06mAmerican Airlines
Deal found 9/9$290
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/139:04 amORD - MKE
Nonstop1h 00mAmerican Airlines
Wed 9/178:00 amMKE - ORD
Nonstop1h 05mAmerican Airlines
Deal found 9/9$300
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:00 pmMDW - MKE
1 stop4h 30mSouthwest
Sun 11/165:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 9/11$301

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago to Milwaukee that are best for you.

Fly from

Chicago

Fly to

Milwaukee

Route

Depart

Return

Price

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 10/8

7:25 pm-8:25 pm

Nonstop1h 00m

Milwaukee-Mitchell

Wed 10/15

8:26 am-9:30 am

Nonstop1h 04m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 11/26

8:51 pm-9:59 pm

Nonstop1h 08m

Milwaukee-Mitchell

Sun 11/30

6:05 am-7:16 am

Nonstop1h 11m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Sun 11/9

7:23 am-8:22 am

Nonstop0h 59m

Milwaukee-Mitchell

Sun 11/16

8:05 am-9:21 am

Nonstop1h 16m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 10/22

9:05 am-10:11 am

Nonstop1h 06m

Milwaukee-Mitchell

Sat 10/25

7:00 am-8:10 am

Nonstop1h 10m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 11/21

12:59 pm-1:58 pm

Nonstop0h 59m

Milwaukee-Mitchell

Sun 11/30

6:05 am-7:16 am

Nonstop1h 11m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 10/10

11:00 pm-11:56 pm

Nonstop0h 56m

Milwaukee-Mitchell

Sun 10/12

8:16 pm-9:30 pm

Nonstop1h 14m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 9/26

9:04 am-10:04 am

Nonstop1h 00m

Milwaukee-Mitchell

Mon 9/29

6:23 pm-7:39 pm

Nonstop1h 16m

$189

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 9/25

9:05 am-10:11 am

Nonstop1h 06m

Milwaukee-Mitchell

Mon 9/29

7:15 pm-8:25 pm

Nonstop1h 10m

$189

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 9/26

9:04 am-10:04 am

Nonstop1h 00m

Milwaukee-Mitchell

Tue 9/30

8:43 am-9:48 am

Nonstop1h 05m

$189

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 9/24

9:04 am-10:04 am

Nonstop1h 00m

Milwaukee-Mitchell

Sun 9/28

5:05 am-6:07 am

Nonstop1h 02m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 36 results
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Best time to book a flight from Chicago to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest time of day to fly from CHI to MKE?

Find hourly flight availability from Chicago to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 18% on flights from Chicago to Milwaukee by exploring options for tickets in the morning.

Weekly flight availability from Chicago to Milwaukee

Explore weekly flight availability from Chicago to Milwaukee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from CHI to MKE are scheduled on a Thursday (52 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (37 on average).

How much does it cost to fly round-trip from Chicago to Milwaukee?

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated September 11, 2025.
Read through reviews of airlines operating flights from Chicago to Milwaukee, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Chicago to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Milwaukee from Chicago?

    Located just 6.4 mi from the city center, Milwaukee-Mitchell is the airport most travelers will use when flying to Milwaukee from Chicago. Booking flights from Chicago to Milwaukee-Mitchell (MKE) should be relatively easy as there are 44 daily inbound flights from Chicago from 1 airline.

  • How long is the flight from Chicago to Milwaukee?

    For as low as $179, American Airlines can have you in Milwaukee from Chicago in 1h. The distance between Chicago and Milwaukee is about 67 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Chicago to Milwaukee round-trip?

    Cheapflights users have booked flights from Chicago to Milwaukee round-trip from $179. American Airlines is priced at 37% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Chicago to Milwaukee?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Milwaukee on time: Qatar Airways (77%), Republic Airways (75%), Copa Airlines (69%).

  • What are the cheapest flights from Chicago to Milwaukee?

    The cheapest flight price from Chicago to Milwaukee is $224. On average you can expect to pay $279. The most popular route, (Chicago O'Hare Intl - Milwaukee-Mitchell), can usually be booked for $179.

  • Can I find deals for flights from Chicago to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Chicago to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Milwaukee.

  • Can I find deals for business class flights from Chicago to Milwaukee?

    Yes. Cheapflights offers flight deals from Chicago to Milwaukee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Milwaukee?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Milwaukee (average of $280). Flying from Chicago to Milwaukee in June is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Oak Creek
New Berlin
Wauwatosa

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Alternative routes for Chicago to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Milwaukee

Discover the top airline that operate flights from Chicago to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$249FlexibilityNo cancel feeOn-time71%

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