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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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
ene. 3 — ene. 101
sáb. 1/3
sáb. 1/10
1 adult, Economy
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Cheap 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 diciembre 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/2. 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.
mar. 12/304:55 pmORD - MKE
Nonstop0h 54mAmerican Airlines
mar. 1/61:04 pmMKE - ORD
Nonstop1h 16mAmerican Airlines
Deal found 12/2$179
This American Airlines deal was found by Cheapflights users on 12/3. 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.
jue. 12/2512:30 pmORD - MKE
Nonstop0h 52mAmerican Airlines
dom. 12/288:08 pmMKE - ORD
Nonstop1h 22mAmerican Airlines
Deal found 12/3$180
This American Airlines deal was found by Cheapflights users on 12/3. 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.
mar. 12/236:29 pmORD - MKE
Nonstop0h 59mAmerican Airlines
sáb. 12/278:08 pmMKE - ORD
Nonstop1h 22mAmerican Airlines
Deal found 12/3$194
This American Airlines deal was found by Cheapflights users on 12/2. 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.
mié. 12/1711:12 amORD - MKE
Nonstop1h 01mAmerican Airlines
dom. 12/216:00 amMKE - ORD
Nonstop1h 20mAmerican Airlines
Deal found 12/2$209
This American Airlines deal was found by Cheapflights users on 12/2. 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.
sáb. 12/134:20 pmORD - MKE
Nonstop0h 56mAmerican Airlines
mié. 12/171:08 pmMKE - ORD
Nonstop1h 12mAmerican Airlines
Deal found 12/2$224
This American Airlines deal was found by Cheapflights users on 12/2. 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.
jue. 12/114:20 pmORD - MKE
Nonstop0h 56mAmerican Airlines
sáb. 12/137:51 pmMKE - ORD
Nonstop1h 23mAmerican Airlines
Deal found 12/2$239
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3111:23 amORD - MKE
1 stop7h 57mMultiple Airlines
mié. 1/78:15 pmMKE - ORD
1 stop21h 37mMultiple Airlines
Deal found 12/3$249
This American Airlines deal was found by Cheapflights users on 12/1. 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.
mié. 12/35:04 pmORD - MKE
Nonstop0h 55mAmerican Airlines
mar. 12/91:08 pmMKE - ORD
Nonstop1h 12mAmerican Airlines
Deal found 12/1$272
This Southwest deal was found by Cheapflights users on 12/2. 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.
jue. 12/116:20 amMDW - MKE
1 stop5h 20mSouthwest
vie. 12/125:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 12/2$284
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
mar. 12/306:50 amORD - MKE
2 stops36h 30mMultiple Airlines
mar. 1/68:15 pmMKE - ORD
1 stop18h 06mMultiple Airlines
Deal found 12/2$285
This American Airlines deal was found by Cheapflights users on 12/3. 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.
jue. 12/45:03 pmORD - MKE
Nonstop0h 55mAmerican Airlines
jue. 12/115:00 amMKE - ORD
Nonstop1h 14mAmerican Airlines
Deal found 12/3$289
This Southwest deal was found by Cheapflights users on 12/3. 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.
jue. 12/116:20 amMDW - MKE
1 stop5h 20mSouthwest
dom. 12/145:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 12/3$309

Find 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 diciembre 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$175
(American Airlines)

One-way from

$68
(Southwest)

Popular in

February

Cheapest in

November

Average price

$394
Provider with most accurate pricing for Chicago (CHI)-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Milwaukee-Mitchell flights.
Search Deals
From Chicago (CHI) to Milwaukee-Mitchell
Search Deals
One-way flight from Chicago (CHI) to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 diciembre 4, 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

mar. 2/3

3:00 pm-3:57 pm

Nonstop0h 57m

Milwaukee-Mitchell

mié. 2/4

6:58 pm-8:20 pm

Nonstop1h 22m

$175

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

vie. 2/13

7:50 pm-8:55 pm

Nonstop1h 05m

Milwaukee-Mitchell

mar. 2/17

5:00 am-6:06 am

Nonstop1h 06m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

mié. 12/31

8:45 am-9:47 am

Nonstop1h 02m

Milwaukee-Mitchell

mié. 1/7

7:32 am-8:53 am

Nonstop1h 21m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

mar. 2/17

10:46 am-11:44 am

Nonstop0h 58m

Milwaukee-Mitchell

vie. 2/27

8:42 am-9:59 am

Nonstop1h 17m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

jue. 1/1

8:45 am-9:47 am

Nonstop1h 02m

Milwaukee-Mitchell

jue. 1/8

1:04 pm-2:20 pm

Nonstop1h 16m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

jue. 12/25

12:30 pm-1:22 pm

Nonstop0h 52m

Milwaukee-Mitchell

dom. 12/28

8:08 pm-9:30 pm

Nonstop1h 22m

$180

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

jue. 3/12

11:00 am-11:45 am

Nonstop0h 45m

Milwaukee-Mitchell

mié. 3/18

5:50 am-6:50 am

Nonstop1h 00m

$208

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

mié. 12/17

11:12 am-12:13 pm

Nonstop1h 01m

Milwaukee-Mitchell

dom. 12/21

6:00 am-7:20 am

Nonstop1h 20m

$209

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

mar. 2/17

2:30 pm-3:35 pm

Nonstop1h 05m

Milwaukee-Mitchell

sáb. 2/21

1:25 pm-2:31 pm

Nonstop1h 06m

$239

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

mié. 2/18

2:30 pm-3:35 pm

Nonstop1h 05m

Milwaukee-Mitchell

sáb. 2/21

11:30 am-12:36 pm

Nonstop1h 06m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 36 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 December.
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 month to book a flight from Chicago to Milwaukee?

Currently, September is the cheapest month in which you can book a flight from Chicago to Milwaukee (average of $178). Flying from Chicago to Milwaukee in March is currently the most expensive (average of $384). 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.

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 diciembre 4, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 49% 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 diciembre 4, 2025.

The most flights from CHI to MKE are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 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 diciembre 4, 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
11,047 reviews

Overall

7.2

Food

6.5

Boarding

7.5

Crew

8.0

Comfort

7.2

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
11,047 reviews
American Airlines
7.2
Good
11,047 reviews

Overall

7.2

Food

6.5

Boarding

7.5

Crew

8.0

Comfort

7.2

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 47 daily inbound flights from Chicago from 2 different airlines.

  • How long is the flight from Chicago to Milwaukee?

    For as low as $175, American Airlines can have you in Milwaukee from Chicago in 57m. 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 32% 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 (81%), United Airlines (75%), Air Canada (72%).

  • 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, September is the cheapest month in which you can book a flight from Chicago to Milwaukee (average of $178). Flying from Chicago to Milwaukee in March is currently the most expensive (average of $384). 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
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 diciembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$239FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$235FlexibilityNo cancel feeOn-time71%

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