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$86+ Cheap flights from Milwaukee (MKE) to Chicago (CHI)

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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
1 adult, Economy
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Cheap flight deals from Milwaukee to Chicago

Cheapest flights from Milwaukee to Chicago
Explore the most affordable flight options available from Milwaukee to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 27, 2026.

This American Airlines deal was found by Cheapflights users on 6/23. 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 7/225:02 am
MKE
-
ORD
Nonstop1h 12m
American Airlines
Wed 7/296:59 am
ORD
-
MKE
Nonstop1h 03m
American Airlines
Deal found 6/23$170
This United Airlines deal was found by Cheapflights users on 6/22. 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 8/57:50 am
MKE
-
ORD
Nonstop1h 10m
United Airlines
Wed 8/125:59 am
ORD
-
MKE
Nonstop1h 08m
United Airlines
Deal found 6/22$171
This Southwest deal was found by Cheapflights users on 6/22. 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 8/53:40 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Wed 8/1210:15 am
MDW
-
MKE
Nonstop0h 50m
Southwest
Deal found 6/22$171
This Southwest deal was found by Cheapflights users on 6/26. 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.
Mon 8/105:45 am
MKE
-
MDW
Nonstop0h 45m
Southwest
Mon 8/178:40 pm
MDW
-
MKE
Nonstop0h 45m
Southwest
Deal found 6/26$175
This United Airlines deal was found by Cheapflights users on 6/25. 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 8/88:50 am
MKE
-
ORD
Nonstop1h 10m
United Airlines
Mon 8/107:45 pm
ORD
-
MKE
Nonstop1h 11m
United Airlines
Deal found 6/25$181
This Southwest deal was found by Cheapflights users on 6/23. 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.
Sat 8/81:30 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Mon 8/108:40 pm
MDW
-
MKE
Nonstop0h 45m
Southwest
Deal found 6/23$181
This Southwest deal was found by Cheapflights users on 6/26. 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.
Thu 8/205:45 am
MKE
-
MDW
Nonstop0h 45m
Southwest
Mon 8/2412:00 pm
MDW
-
MKE
1 stop3h 40m
Southwest
Deal found 6/26$185
This American Airlines deal was found by Cheapflights users on 6/25. 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 8/205:00 am
MKE
-
ORD
Nonstop1h 14m
American Airlines
Mon 8/247:58 pm
ORD
-
MKE
Nonstop1h 02m
American Airlines
Deal found 6/25$191
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Tue 7/216:20 am
MKE
-
ORD
Nonstop1h 10m
United Airlines
Fri 7/246:15 pm
ORD
-
MKE
Nonstop1h 11m
United Airlines
Deal found 6/23$195
This Southwest deal was found by Cheapflights users on 6/24. 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 7/214:10 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Thu 7/239:55 pm
MDW
-
MKE
Nonstop0h 55m
Southwest
Deal found 6/24$195
This Southwest deal was found by Cheapflights users on 6/26. 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.
Sat 8/151:30 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Sun 8/166:15 pm
MDW
-
MKE
Nonstop0h 50m
Southwest
Deal found 6/26$204
This United Airlines deal was found by Cheapflights users on 6/23. 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 9/37:18 am
MKE
-
ORD
Nonstop1h 11m
United Airlines
Fri 9/45:59 am
ORD
-
MKE
Nonstop1h 08m
United Airlines
Deal found 6/23$205

Find flight deals from Milwaukee to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Chicago (CHI). 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 June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$170
(American Airlines)

One-way from

$86
(United Airlines)

Good round-trip deal

$359 or less

Good one-way deal

$168 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Chicago (CHI) flights.
Search Deals
From Milwaukee-Mitchell to Chicago (CHI)
Search Deals
One-way flight from Milwaukee-Mitchell to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Milwaukee-Mitchell to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Milwaukee-Mitchell to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee to Chicago 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 June 27, 2026.
Use the filters below to find and compare flights from Milwaukee to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 8/5

7:50 am-9:00 am

Nonstop1h 10m

Chicago O'Hare Intl

Wed 8/12

5:59 am-7:07 am

Nonstop1h 08m

$171

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 8/5

6:48 pm-8:21 pm

Nonstop1h 33m

Chicago O'Hare Intl

Wed 8/12

6:56 pm-7:59 pm

Nonstop1h 03m

$171

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 8/5

3:40 pm-4:30 pm

Nonstop0h 50m

Chicago Midway

Wed 8/12

10:15 am-11:05 am

Nonstop0h 50m

$171

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 8/26

11:18 am-12:29 pm

Nonstop1h 11m

Chicago O'Hare Intl

Wed 9/2

4:05 pm-5:15 pm

Nonstop1h 10m

$171
Quickest round-trip

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 8/10

5:45 am-6:30 am

Nonstop0h 45m

Chicago Midway

Mon 8/17

8:40 pm-9:25 pm

Nonstop0h 45m

$175

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 8/8

1:30 pm-2:20 pm

Nonstop0h 50m

Chicago Midway

Mon 8/10

8:40 pm-9:25 pm

Nonstop0h 45m

$181

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 8/20

5:45 am-6:30 am

Nonstop0h 45m

Chicago Midway

Mon 8/24

12:00 pm-3:40 pm

1 stop3h 40m

$185

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 7/21

6:20 am-7:30 am

Nonstop1h 10m

Chicago O'Hare Intl

Fri 7/24

6:15 pm-7:26 pm

Nonstop1h 11m

$195

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sat 8/15

10:19 am-11:30 am

Nonstop1h 11m

Chicago O'Hare Intl

Sun 8/16

8:50 am-10:00 am

Nonstop1h 10m

$195

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 7/28

4:10 pm-5:00 pm

Nonstop0h 50m

Chicago Midway

Thu 7/30

9:55 pm-10:50 pm

Nonstop0h 55m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

Showing 1-10 of 41 resultsSorted by cheapest first
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5

Compare providers for flights from Milwaukee to Chicago

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 Milwaukee to Chicago in June.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 Milwaukee-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Chicago 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 Milwaukee-Chicago 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 Milwaukee to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Milwaukee 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 Milwaukee to Chicago

What is the cheapest time of day to fly from MKE to CHI?

Find hourly flight availability from Milwaukee to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 27, 2026.

It’s optimal to fly from Milwaukee to Chicago in the morning. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the evening.

Weekly flight availability from Milwaukee to Chicago

Explore weekly flight availability from Milwaukee to Chicago. 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 June 27, 2026.

The most flights from MKE to CHI are scheduled on a Friday (56 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (20 on average).

How often are flights from Milwaukee to Chicago delayed?

About 13% of weekly flights between Milwaukee and Chicago have experienced delays in the past year, with the average delay time being 123 minutes.

What is the most punctual flight time for Milwaukee to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Milwaukee to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 11% of flights being delayed.

What is the cheapest day to fly from Milwaukee to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Chicago. Price data was last updated on June 20, 2026.

Travelers seeking maximum savings on their Milwaukee to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 27, 2026.
Read reviews from past customers who have flown American Airlines from Milwaukee to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,779 reviews

Boarding

7.5

Entertainment

6.8

Food

6.4

Overall

7.1

Crew

7.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,779 reviews
American Airlines
7.1
Good
11,779 reviews

Boarding

7.5

Entertainment

6.8

Food

6.4

Overall

7.1

Crew

7.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Milwaukee to Chicago. 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 from for flights from Milwaukee to Chicago?

    Milwaukee-Mitchell (MKE) is the airport you will fly out of if you book a flight from Milwaukee to Chicago. You should not have trouble finding flights to Chicago from Milwaukee-Mitchell; the airport handles an average of 45 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights from the Milwaukee airport to Chicago. It is only a 6.4 mi journey to Milwaukee-Mitchell (MKE) from Milwaukee’s city center.

  • How long is the flight from Milwaukee to Chicago?

    For as low as $171, United Airlines can have you in Chicago from Milwaukee in 50m. The distance between Milwaukee and Chicago is about 80 mi. All flights are typically nonstop.

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

    Cheapflights users have booked flights from Milwaukee to Chicago round-trip from $179. Another airline that can offer you cheap pricing is United Airlines.

  • What are the most reliable airlines from Milwaukee to Chicago?

    No one likes to see their flight delayed. When booking a flight from Milwaukee to Chicago consider choosing Japan Airlines (72%), Aer Lingus (70%) or American Airlines (69%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Milwaukee to Chicago?

    Looking for the cheapest flight from Milwaukee to Chicago? While on average our users pay $1,007, our data indicates the cheapest price to be $134. The most popular route (Milwaukee-Mitchell - Chicago O'Hare Intl), is priced around $171.

  • Can I find deals for flights from Milwaukee to Chicago that include hotel bookings?

    Yes. In addition to deals on Milwaukee to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Milwaukee to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Milwaukee to Chicago.

  • Can I find deals for business class flights from Milwaukee to Chicago?

    Yes. Cheapflights offers flight deals from Milwaukee to Chicago 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 2 airlines flying from Milwaukee to Chicago

Discover the top 2 airlines that operate flights from Milwaukee to Chicago. 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 June 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$219FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$219FlexibilityNo cancel feeOn-time69%

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