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$89+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$89
(FlightHub)

Popular in

December

Cheapest in

April

Average price

$473

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. 21% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This United Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 9/42:03 pmORD - MKE
Nonstop1h 06mUnited Airlines
Mon 9/87:15 pmMKE - ORD
Nonstop1h 10mUnited Airlines
Deal found 8/14$179
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 9/45:53 pmORD - MKE
Nonstop0h 53mAmerican Airlines
Sun 9/76:18 amMKE - ORD
Nonstop1h 06mAmerican Airlines
Deal found 8/14$180
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/26:15 pmORD - MKE
Nonstop1h 03mAmerican Airlines
Tue 9/98:43 amMKE - ORD
Nonstop1h 05mAmerican Airlines
Deal found 8/13$184
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 9/119:35 pmORD - MKE
Nonstop1h 06mUnited Airlines
Thu 9/186:00 amMKE - ORD
Nonstop1h 10mUnited Airlines
Deal found 8/14$194
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/276:55 pmORD - MKE
Nonstop1h 05mAmerican Airlines
Sat 8/308:05 amMKE - ORD
Nonstop1h 04mAmerican Airlines
Deal found 8/14$199
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1910:42 amORD - MKE
1 stop7h 59mFrontier
Sun 9/213:03 pmMKE - ORD
1 stop8h 56mFrontier
Deal found 8/14$225
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/59:06 amORD - MKE
Nonstop1h 00mAmerican Airlines
Sun 9/76:18 amMKE - ORD
Nonstop1h 06mAmerican Airlines
Deal found 8/13$239
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 9/48:50 pmORD - MKE
Nonstop1h 06mUnited Airlines
Sun 9/77:00 amMKE - ORD
Nonstop1h 10mUnited Airlines
Deal found 8/14$241
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 8/146:55 pmORD - MKE
Nonstop1h 05mAmerican Airlines
Wed 8/201:06 pmMKE - ORD
Nonstop1h 04mAmerican Airlines
Deal found 8/13$259
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/1611:40 amORD - MKE
Nonstop0h 56mAmerican Airlines
Sun 8/177:49 pmMKE - ORD
Nonstop1h 04mAmerican Airlines
Deal found 8/14$290
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 8/148:14 pmORD - MKE
Nonstop1h 05mAmerican Airlines
Sat 8/169:58 amMKE - ORD
Nonstop1h 04mAmerican Airlines
Deal found 8/14$293
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sat 9/2710:51 amMDW - MKE
1 stop25h 07mMultiple Airlines
Sun 10/2612:42 pmMKE - MDW
2 stops10h 43mMultiple Airlines
Deal found 8/14$370

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 August 14, 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

Thu 9/4

10:00 am-10:57 am

Nonstop0h 57m

Milwaukee-Mitchell

Sun 9/7

5:05 am-6:07 am

Nonstop1h 02m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 9/10

9:04 am-10:04 am

Nonstop1h 00m

Milwaukee-Mitchell

Sat 9/13

6:18 am-7:24 am

Nonstop1h 06m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 9/10

9:04 am-10:04 am

Nonstop1h 00m

Milwaukee-Mitchell

Wed 9/17

10:34 am-11:40 am

Nonstop1h 06m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 10/9

3:37 pm-4:29 pm

Nonstop0h 52m

Milwaukee-Mitchell

Sun 10/12

2:18 pm-3:27 pm

Nonstop1h 09m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Tue 9/2

6:55 pm-8:00 pm

Nonstop1h 05m

Milwaukee-Mitchell

Tue 9/9

4:37 pm-5:49 pm

Nonstop1h 12m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Sat 9/27

9:04 am-10:04 am

Nonstop1h 00m

Milwaukee-Mitchell

Sun 10/26

8:29 am-9:33 am

Nonstop1h 04m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 9/19

9:04 am-10:04 am

Nonstop1h 00m

Milwaukee-Mitchell

Sun 9/21

5:05 am-6:07 am

Nonstop1h 02m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 9/4

5:53 pm-6:46 pm

Nonstop0h 53m

Milwaukee-Mitchell

Thu 9/18

4:33 pm-5:45 pm

Nonstop1h 12m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Tue 9/9

6:56 pm-8:00 pm

Nonstop1h 04m

Milwaukee-Mitchell

Tue 9/16

10:34 am-11:40 am

Nonstop1h 06m

$179

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 9/27

10:51 am-11:58 am

1 stop25h 07m

Milwaukee-Mitchell

Sun 10/26

12:42 pm-11:25 pm

2 stops10h 43m

$370

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 22 results
1
2
3

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 August 14, 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 August 14, 2025.

The most flights from CHI to MKE are scheduled on a Friday (51 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (17 on average).

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 August 14, 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

Boarding

7.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Crew

8.0

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Crew

8.0

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 43 daily inbound flights from Chicago from 1 airline.

  • 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 39% 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: Republic Airways (88%), United Airlines (69%), Copa Airlines (68%).

  • 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
Mequon
Oak Creek
Sheboygan
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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$249FlexibilityNo cancel feeOn-time71%

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