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$91+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
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 May 5, 2026.

This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:30 am
MKE
-
ORD
Nonstop1h 11m
United Airlines
Tue 9/19:30 pm
ORD
-
MKE
Nonstop1h 06m
United Airlines
Deal found 5/1$181
This Southwest deal was found by Cheapflights users on 5/3. 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 6/174:10 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Wed 6/2410:10 am
MDW
-
MKE
Nonstop0h 45m
Southwest
Deal found 5/3$181
This American Airlines deal was found by Cheapflights users on 5/3. 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.
Wed 6/171:28 pm
MKE
-
ORD
Nonstop1h 15m
American Airlines
Wed 6/248:00 pm
ORD
-
MKE
Nonstop1h 05m
American Airlines
Deal found 5/3$182
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.
Mon 5/256:45 pm
MKE
-
ORD
Nonstop1h 27m
American Airlines
Wed 5/275:16 pm
ORD
-
MKE
Nonstop0h 59m
American Airlines
Deal found 4/30$191
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/21:44 pm
MKE
-
ORD
Nonstop1h 16m
American Airlines
Tue 6/96:40 am
ORD
-
MKE
Nonstop1h 02m
American Airlines
Deal found 5/5$197
This Southwest deal was found by Cheapflights users on 5/4. 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.
Tue 6/306:00 am
MKE
-
MDW
Nonstop0h 50m
Southwest
Tue 7/145:20 pm
MDW
-
MKE
1 stop5h 50m
Southwest
Deal found 5/4$199
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.
Wed 5/278:12 am
MKE
-
ORD
Nonstop1h 19m
American Airlines
Sun 5/319:21 pm
ORD
-
MKE
Nonstop1h 03m
American Airlines
Deal found 4/30$200
This Southwest deal was found by Cheapflights users on 5/3. 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 6/176:00 am
MKE
-
MDW
Nonstop0h 50m
Southwest
Thu 6/189:55 pm
MDW
-
MKE
Nonstop0h 50m
Southwest
Deal found 5/3$200
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.
Thu 5/281:43 pm
MKE
-
ORD
Nonstop1h 16m
American Airlines
Thu 6/49:20 pm
ORD
-
MKE
Nonstop1h 04m
American Airlines
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.
Thu 5/284:50 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Thu 6/410:20 am
MDW
-
MKE
Nonstop0h 45m
Southwest
Deal found 4/30$201
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:00 am
MKE
-
ORD
Nonstop1h 14m
American Airlines
Mon 6/86:40 am
ORD
-
MKE
Nonstop1h 02m
American Airlines
Deal found 5/4$202
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Tue 5/268:46 am
MKE
-
ORD
2 stops23h 09m
Frontier
Wed 6/35:11 pm
ORD
-
MKE
1 stop14h 50m
Frontier
Deal found 5/4$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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(United Airlines)

One-way from

$91
(American Airlines)

Good round-trip deal

$336 or less

Good one-way deal

$201 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 May 5, 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

Tue 6/2

5:00 am-6:14 am

Nonstop1h 14m

Chicago O'Hare Intl

Tue 6/9

6:59 pm-7:58 pm

Nonstop0h 59m

$181

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 6/17

8:50 am-10:00 am

Nonstop1h 10m

Chicago O'Hare Intl

Wed 6/24

6:29 pm-7:40 pm

Nonstop1h 11m

$181
Quickest round-trip

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 6/17

4:10 pm-5:00 pm

Nonstop0h 50m

Chicago Midway

Wed 6/24

10:10 am-10:55 am

Nonstop0h 45m

$181

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 6/2

8:12 am-9:31 am

Nonstop1h 19m

Chicago O'Hare Intl

Sat 6/6

6:59 pm-7:58 pm

Nonstop0h 59m

$191

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 5/27

5:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Sun 5/31

9:40 pm-10:25 pm

Nonstop0h 45m

$209

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 6/1

7:25 am-8:29 am

Nonstop1h 04m

Chicago O'Hare Intl

Sun 6/7

3:40 pm-4:46 pm

Nonstop1h 06m

$210

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sat 6/6

8:00 am-9:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Sat 6/20

5:17 pm-6:25 pm

Nonstop1h 08m

$210

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 5/31

5:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Mon 6/8

9:55 pm-10:45 pm

Nonstop0h 50m

$210

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 6/27

4:00 pm-4:50 pm

Nonstop0h 50m

Chicago Midway

Sat 6/27

8:55 pm-9:45 pm

Nonstop0h 50m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 6/4

5:40 am-6:30 am

Nonstop0h 50m

Chicago Midway

Thu 6/11

6:40 pm-12:15 am

1 stop5h 35m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 39 resultsSorted by cheapest first
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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 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 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 month to book a flight from Milwaukee to Chicago?

Currently, January is the cheapest month in which you can book a flight from Milwaukee to Chicago (average of $179). Flying from Milwaukee to Chicago in November is currently the most expensive (average of $284). 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 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 May 5, 2026.

It’s optimal to fly from Milwaukee to Chicago in the morning. By choosing this option you can save up to 37% on the cost of your flight, compared to a flight in the evening.

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 May 2, 2026.

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

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 May 5, 2026.

The most flights from MKE to CHI are scheduled on a Monday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 122 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 evening tend to experience delays more often.

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

Wednesday tends to have the lowest number of delays on this route, whereas Friday 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.

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 May 5, 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
11,667 reviews

Comfort

7.2

Overall

7.1

Food

6.4

Crew

7.9

Entertainment

6.9

Boarding

7.5

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
11,667 reviews
American Airlines
7.1
Good
11,667 reviews

Comfort

7.2

Overall

7.1

Food

6.4

Crew

7.9

Entertainment

6.9

Boarding

7.5

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 57 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 $181, American 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 Alaska Airlines (59%), Aer Lingus (59%) or Envoy Air (57%) 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 $716, our data indicates the cheapest price to be $137. The most popular route (Milwaukee-Mitchell - Chicago O'Hare Intl), is priced around $181.

  • 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.

  • What is the cheapest month to book a flight from Milwaukee to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Milwaukee to Chicago (average of $179). Flying from Milwaukee to Chicago in November is currently the most expensive (average of $284). 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 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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$191FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$224FlexibilityNo cancel feeOn-time69%

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