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$91+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
May 31 — Jun 71
Sun 5/31
Sun 6/7
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 May 1, 2026.

This Southwest deal was found by Cheapflights users on 4/26. 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 5/2010:10 am
MDW
-
MKE
Nonstop0h 45m
Southwest
Wed 6/35:50 am
MKE
-
MDW
Nonstop0h 55m
Southwest
Deal found 4/26$181
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/206:40 am
ORD
-
MKE
Nonstop1h 02m
American Airlines
Tue 6/236:50 pm
MKE
-
ORD
Nonstop1h 24m
American Airlines
Deal found 4/30$200
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Mon 5/257:50 pm
ORD
-
MKE
Nonstop1h 06m
United Airlines
Mon 6/110:38 am
MKE
-
ORD
Nonstop1h 10m
United Airlines
Deal found 4/27$201
This Southwest deal was found by Cheapflights users on 4/30. 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 5/219:30 pm
MDW
-
MKE
Nonstop0h 45m
Southwest
Mon 5/254:50 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 4/30$201
This Southwest deal was found by Cheapflights users on 4/30. 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 6/1710:10 am
MDW
-
MKE
Nonstop0h 45m
Southwest
Tue 6/236:00 am
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 4/30$209
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/229:25 pm
ORD
-
MKE
Nonstop1h 03m
American Airlines
Mon 5/258:12 am
MKE
-
ORD
Nonstop1h 19m
American Airlines
Deal found 4/28$210
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/249:21 pm
ORD
-
MKE
Nonstop1h 03m
American Airlines
Fri 5/297:30 am
MKE
-
ORD
Nonstop1h 19m
American Airlines
Deal found 4/27$219
This Southwest deal was found by Cheapflights users on 4/28. 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 5/2910:10 am
MDW
-
MKE
Nonstop0h 45m
Southwest
Fri 6/55:15 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 4/28$219
This American Airlines deal was found by Cheapflights users on 4/27. 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 6/116:59 pm
ORD
-
MKE
Nonstop0h 59m
American Airlines
Thu 6/1810:00 am
MKE
-
ORD
Nonstop1h 12m
American Airlines
Deal found 4/27$220
This American Airlines deal was found by Cheapflights users on 4/30. 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 7/186:55 am
ORD
-
MKE
Nonstop1h 03m
American Airlines
Sun 7/197:03 pm
MKE
-
ORD
Nonstop1h 34m
American Airlines
Deal found 4/30$228
This Southwest deal was found by Cheapflights users on 4/30. 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 6/129:55 pm
MDW
-
MKE
Nonstop0h 50m
Southwest
Mon 6/155:15 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 4/30$228
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 6/158:00 pm
ORD
-
MKE
Nonstop1h 05m
American Airlines
Mon 6/228:00 am
MKE
-
ORD
Nonstop1h 10m
American Airlines
Deal found 5/1$229

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 May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(Southwest)

One-way from

$91
(American Airlines)

Good round-trip deal

$181 or less

Good one-way deal

$199 or less
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
Price to beat on a round-trip flight from Chicago (CHI) to Milwaukee-Mitchell.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Milwaukee-Mitchell.
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 May 1, 2026.
Use the filters below to find and compare flights from Chicago to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 5/20

10:10 am-10:55 am

Nonstop0h 45m

Milwaukee-Mitchell

Wed 6/3

5:50 am-6:45 am

Nonstop0h 55m

$181

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Mon 6/1

8:02 pm-9:04 pm

Nonstop1h 02m

Milwaukee-Mitchell

Fri 6/5

8:00 am-9:10 am

Nonstop1h 10m

$210

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Thu 6/11

8:49 am-9:57 am

Nonstop1h 08m

Milwaukee-Mitchell

Sat 6/13

7:00 pm-8:11 pm

Nonstop1h 11m

$219

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 5/15

10:30 am-11:31 am

Nonstop1h 01m

Milwaukee-Mitchell

Sun 5/17

6:49 am-7:58 am

Nonstop1h 09m

$248

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Tue 6/9

11:55 am-12:55 pm

Nonstop1h 00m

Milwaukee-Mitchell

Wed 6/10

1:30 pm-2:40 pm

Nonstop1h 10m

$251

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 6/17

5:10 pm-10:25 pm

1 stop5h 15m

Milwaukee-Mitchell

Tue 6/23

12:25 pm-5:10 pm

1 stop4h 45m

$259

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Mon 6/15

6:40 pm-7:51 pm

Nonstop1h 11m

Milwaukee-Mitchell

Wed 6/17

10:38 am-11:48 am

Nonstop1h 10m

$263

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 6/11

9:55 pm-10:45 pm

Nonstop0h 50m

Milwaukee-Mitchell

Thu 6/18

7:20 am-1:45 pm

1 stop6h 25m

$268

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Sun 6/21

4:47 pm-5:53 pm

Nonstop1h 06m

Milwaukee-Mitchell

Wed 6/24

5:29 pm-6:40 pm

Nonstop1h 11m

$270

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 6/19

4:47 pm-5:53 pm

Nonstop1h 06m

Milwaukee-Mitchell

Tue 6/23

5:00 am-6:10 am

Nonstop1h 10m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 39 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 May 1, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 35% on flights from Chicago to Milwaukee by exploring options for tickets in the afternoon.

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 May 1, 2026.

The most flights from CHI to MKE are scheduled on a Friday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).

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 50 daily inbound flights from Chicago from 2 different airlines.

  • How long is the flight from Chicago to Milwaukee?

    For as low as $181, Southwest can have you in Milwaukee from Chicago in 45m. The distance between Chicago and Milwaukee is about 80 mi. All flights are typically nonstop.

  • 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.

  • 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: Envoy Air (75%), Lufthansa (70%), PSA Airlines (62%).

  • What are the cheapest flights from Chicago to Milwaukee?

    The cheapest flight price from Chicago to Milwaukee is $85. On average you can expect to pay $223. The most popular route, (Chicago O'Hare Intl - Milwaukee-Mitchell), can usually be booked for $200.

  • 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
Port Washington
New Berlin
Oak Creek
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$318FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$224FlexibilityNo cancel feeOn-time71%

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