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$97+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$97
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$179

Good round-trip deal

$179 or less
Provider with most accurate pricing for Chicago (CHI)-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Milwaukee-Mitchell flights.
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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. 12% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip 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 November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/3. 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 12/24:49 pmORD - MKE
Nonstop0h 54mAmerican Airlines
Tue 12/94:30 pmMKE - ORD
Nonstop1h 13mAmerican Airlines
Deal found 11/3$179
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Mon 12/229:05 amORD - MKE
Nonstop1h 08mAmerican Airlines
Sun 1/47:45 amMKE - ORD
Nonstop1h 18mAmerican Airlines
Deal found 11/3$183
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/2010:20 amORD - MKE
Nonstop1h 04mUnited Airlines
Mon 11/246:05 amMKE - ORD
Nonstop1h 11mUnited Airlines
Deal found 11/5$209
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 12/47:00 amORD - MKE
2 stops34h 09mMultiple Airlines
Thu 12/1110:34 amMKE - ORD
1 stop11h 14mMultiple Airlines
Deal found 11/5$212
This Southwest deal was found by Cheapflights users on 11/5. 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.
Thu 12/412:15 pmMDW - MKE
1 stop4h 35mSouthwest
Thu 12/115:30 amMKE - MDW
1 stop7h 15mSouthwest
Deal found 11/5$219
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Wed 12/34:58 pmORD - MKE
2 stops16h 41mMultiple Airlines
Fri 12/56:09 pmMKE - ORD
1 stop19h 07mMultiple Airlines
Deal found 11/4$220
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/204:55 pmORD - MKE
Nonstop0h 54mAmerican Airlines
Sat 12/278:08 pmMKE - ORD
Nonstop1h 22mAmerican Airlines
Deal found 11/5$235
This Southwest deal was found by Cheapflights users on 11/4. 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.
Wed 12/310:05 amMDW - MKE
1 stop6h 45mSouthwest
Fri 12/54:05 pmMKE - MDW
1 stop4h 40mSouthwest
Deal found 11/4$239
This United Airlines deal was found by Cheapflights users on 11/6. 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 11/272:05 pmORD - MKE
Nonstop1h 02mUnited Airlines
Sun 11/307:00 amMKE - ORD
Nonstop1h 11mUnited Airlines
Deal found 11/6$240
This Southwest deal was found by Cheapflights users on 11/5. 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.
Tue 12/29:50 amMDW - MKE
1 stop5h 35mSouthwest
Tue 12/235:50 amMKE - MDW
1 stop4h 15mSouthwest
Deal found 11/5$267
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:20 amORD - MKE
2 stops25h 19mSpirit Airlines
Fri 12/510:34 amMKE - ORD
2 stops13h 35mSpirit Airlines
Deal found 11/4$268
This Southwest deal was found by Cheapflights users on 11/3. 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.
Wed 12/179:50 amMDW - MKE
1 stop5h 35mSouthwest
Fri 1/26:30 pmMKE - MDW
1 stop3h 15mSouthwest
Deal found 11/3$268

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 November 6, 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 12/4

9:32 pm-10:30 pm

Nonstop0h 58m

Milwaukee-Mitchell

Thu 12/11

8:40 am-9:51 am

Nonstop1h 11m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 12/17

7:00 am-7:58 am

Nonstop0h 58m

Milwaukee-Mitchell

Fri 1/2

8:08 pm-9:30 pm

Nonstop1h 22m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 11/26

9:45 pm-10:43 pm

Nonstop0h 58m

Milwaukee-Mitchell

Sun 11/30

7:00 am-8:11 am

Nonstop1h 11m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 1/22

2:59 pm-3:56 pm

Nonstop0h 57m

Milwaukee-Mitchell

Sun 1/25

1:04 pm-2:20 pm

Nonstop1h 16m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Tue 12/2

4:49 pm-5:43 pm

Nonstop0h 54m

Milwaukee-Mitchell

Tue 12/9

4:30 pm-5:43 pm

Nonstop1h 13m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 11/27

10:23 am-11:29 am

Nonstop1h 06m

Milwaukee-Mitchell

Sun 11/30

12:05 pm-1:15 pm

Nonstop1h 10m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Tue 12/2

10:01 pm-11:06 pm

Nonstop1h 05m

Milwaukee-Mitchell

Tue 12/23

8:02 pm-9:24 pm

Nonstop1h 22m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 1/2

4:55 pm-5:49 pm

Nonstop0h 54m

Milwaukee-Mitchell

Thu 1/8

6:58 pm-8:20 pm

Nonstop1h 22m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 12/19

12:25 pm-1:22 pm

Nonstop0h 57m

Milwaukee-Mitchell

Fri 12/26

8:08 pm-9:30 pm

Nonstop1h 22m

$180

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 12/4

12:15 pm-4:50 pm

1 stop4h 35m

Milwaukee-Mitchell

Thu 12/11

5:30 am-12:45 pm

1 stop7h 15m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 35 results
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Compare providers for flights from Chicago to Milwaukee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Milwaukee in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Milwaukee flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Milwaukee flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Milwaukee flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 November 6, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 45% on flights from Chicago to Milwaukee by exploring options for tickets in the evening.

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 November 6, 2025.

The most flights from CHI to MKE are scheduled on a Thursday (54 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (33 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 November 6, 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
11,040 reviews

Food

6.4

Comfort

7.2

Boarding

7.5

Overall

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Food

6.4

Comfort

7.2

Boarding

7.5

Overall

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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 2 different airlines.

  • How long is the flight from Chicago to Milwaukee?

    For as low as $179, United Airlines can have you in Milwaukee from Chicago in 58m. The distance between Chicago and Milwaukee is about 67 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Milwaukee round-trip?

    Cheapflights users have booked flights from Chicago to Milwaukee round-trip from $179. Another airline that can offer you cheap pricing is United Airlines. American Airlines is priced at 33% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Milwaukee one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $109. Southwest flights start at $110 while deals on Spirit Airlines start at $120 one-way.

  • 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 (96%), Emirates (82%), United Airlines (81%).

  • What are the cheapest flights from Chicago to Milwaukee?

    The cheapest flight price from Chicago to Milwaukee is $179. On average you can expect to pay $179. 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.

See more FAQs

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
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 2 airlines flying from Chicago to Milwaukee

Discover the top 2 airlines 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$235FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$239FlexibilityNo cancel feeOn-time69%

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