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$110+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
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 October 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$110
(Southwest)

Popular in

December

Cheapest in

September

Average price

$304

Good round-trip deal

$184 or less

Good one-way deal

$279 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. 21% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Milwaukee-Mitchell.
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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 October 10, 2025.

This United Airlines deal was found by Cheapflights users on 10/8. 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.
Fri 11/710:20 amORD - MKE
Nonstop1h 04mUnited Airlines
Fri 11/143:49 pmMKE - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/8$179
This American Airlines deal was found by Cheapflights users on 10/9. 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.
Thu 10/309:27 amORD - MKE
Nonstop1h 06mAmerican Airlines
Sun 11/212:09 pmMKE - ORD
Nonstop1h 09mAmerican Airlines
Deal found 10/9$180
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/248:20 pmORD - MKE
Nonstop1h 04mAmerican Airlines
Wed 10/299:30 amMKE - ORD
Nonstop1h 05mAmerican Airlines
Deal found 10/7$184
This United Airlines deal was found by Cheapflights users on 10/7. 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 10/2210:20 amORD - MKE
Nonstop1h 06mUnited Airlines
Sun 10/267:00 amMKE - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/7$189
This American Airlines deal was found by Cheapflights users on 10/8. 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 10/1512:53 pmORD - MKE
Nonstop0h 55mAmerican Airlines
Wed 10/222:18 pmMKE - ORD
Nonstop1h 09mAmerican Airlines
Deal found 10/8$199
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 10/183:37 pmORD - MKE
Nonstop0h 52mAmerican Airlines
Tue 10/214:59 pmMKE - ORD
Nonstop1h 11mAmerican Airlines
Deal found 10/8$209
This American Airlines deal was found by Cheapflights users on 10/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/42:33 pmORD - MKE
Nonstop1h 00mAmerican Airlines
Tue 11/115:00 amMKE - ORD
Nonstop1h 10mAmerican Airlines
Deal found 10/6$224
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:20 amORD - MKE
Nonstop1h 04mUnited Airlines
Sun 11/210:53 amMKE - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/9$238
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 10/249:40 amMDW - MKE
1 stop3h 25mSouthwest
Wed 10/295:45 amMKE - MDW
1 stop4h 10mSouthwest
Deal found 10/7$238
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:35 pmORD - MKE
Nonstop0h 57mUnited Airlines
Sun 11/96:05 amMKE - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/9$239
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 10/119:25 pmORD - MKE
Nonstop1h 06mUnited Airlines
Tue 10/143:44 pmMKE - ORD
Nonstop1h 10mUnited Airlines
Deal found 10/6$240
This Southwest deal was found by Cheapflights users on 10/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:40 amMDW - MKE
1 stop5h 25mSouthwest
Sun 11/25:00 amMKE - MDW
1 stop4h 55mSouthwest
Deal found 10/6$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 October 10, 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

Tue 11/4

9:45 pm-10:43 pm

Nonstop0h 58m

Milwaukee-Mitchell

Tue 11/11

6:05 am-7:16 am

Nonstop1h 11m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 10/31

12:53 pm-1:48 pm

Nonstop0h 55m

Milwaukee-Mitchell

Mon 11/3

6:57 pm-8:18 pm

Nonstop1h 21m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 11/7

10:20 am-11:24 am

Nonstop1h 04m

Milwaukee-Mitchell

Fri 11/14

3:49 pm-5:00 pm

Nonstop1h 11m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 10/30

8:20 pm-9:24 pm

Nonstop1h 04m

Milwaukee-Mitchell

Sun 11/2

6:57 pm-8:18 pm

Nonstop1h 21m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Mon 12/1

12:59 pm-1:58 pm

Nonstop0h 59m

Milwaukee-Mitchell

Sat 12/27

5:42 pm-6:55 pm

Nonstop1h 13m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 11/5

7:00 am-7:55 am

Nonstop0h 55m

Milwaukee-Mitchell

Wed 11/12

9:05 am-10:17 am

Nonstop1h 12m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 10/24

8:20 pm-9:24 pm

Nonstop1h 04m

Milwaukee-Mitchell

Wed 10/29

9:30 am-10:35 am

Nonstop1h 05m

$184

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 10/22

10:20 am-11:26 am

Nonstop1h 06m

Milwaukee-Mitchell

Sun 10/26

7:00 am-8:11 am

Nonstop1h 11m

$189

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 10/23

9:05 am-10:11 am

Nonstop1h 06m

Milwaukee-Mitchell

Mon 10/27

2:45 pm-3:56 pm

Nonstop1h 11m

$189

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 10/24

5:50 pm-6:56 pm

Nonstop1h 06m

Milwaukee-Mitchell

Tue 10/28

12:04 pm-1:15 pm

Nonstop1h 11m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 38 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Milwaukee flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 October 10, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 54% 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 October 10, 2025.

The most flights from CHI to MKE are scheduled on a Wednesday (56 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (50 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 October 10, 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
11,043 reviews

Comfort

7.2

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

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
11,043 reviews
American Airlines
7.2
Good
11,043 reviews

Comfort

7.2

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

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 53 daily inbound flights from Chicago from 1 airline.

  • How long is the flight from Chicago to Milwaukee?

    For as low as $179, United Airlines can have you in Milwaukee from Chicago in 55m. 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 38% 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: Air New Zealand (75%), Air Canada (73%), ANA (73%).

  • 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 $265. 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
Oak Creek
New Berlin
Wauwatosa

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Alternative routes for Chicago to Milwaukee

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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 October 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$235FlexibilityNo cancel feeOn-time71%

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