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$88+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$88
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$222

Good round-trip deal

$318 or less

Good one-way deal

$170 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Chicago (CHI) flights.
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From Milwaukee-Mitchell to Chicago (CHI)
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One-way flight from Milwaukee-Mitchell to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($20 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 Milwaukee-Mitchell to Chicago (CHI).
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Price to beat on a one-way flight from Milwaukee-Mitchell to Chicago (CHI).
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Find 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 October 30, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:05 pmMKE - ORD
Nonstop1h 10mUnited Airlines
Fri 11/285:50 pmORD - MKE
Nonstop0h 57mUnited Airlines
Deal found 10/28$179
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/165:00 amMKE - ORD
Nonstop1h 10mAmerican Airlines
Sun 11/2310:01 pmORD - MKE
Nonstop1h 05mAmerican Airlines
Deal found 10/29$194
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:53 amMKE - ORD
Nonstop1h 11mUnited Airlines
Fri 11/1410:20 amORD - MKE
Nonstop1h 04mUnited Airlines
Deal found 10/28$204
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/135:00 amMKE - ORD
Nonstop1h 10mAmerican Airlines
Mon 11/175:34 pmORD - MKE
Nonstop0h 53mAmerican Airlines
Deal found 10/29$209
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:05 pmMKE - ORD
Nonstop1h 10mUnited Airlines
Sun 11/99:45 pmORD - MKE
Nonstop0h 58mUnited Airlines
Deal found 10/28$239
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2712:35 pmMKE - ORD
1 stop10h 31mSpirit Airlines
Thu 12/41:52 pmORD - MKE
2 stops19h 47mSpirit Airlines
Deal found 10/30$240
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:30 pmMKE - ORD
1 stop16h 09mMultiple Airlines
Wed 12/38:00 amORD - MKE
2 stops25h 39mMultiple Airlines
Deal found 10/27$247
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/76:09 pmMKE - ORD
1 stop20h 12mMultiple Airlines
Fri 12/127:20 amORD - MKE
1 stop9h 49mMultiple Airlines
Deal found 10/29$248
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 11/266:35 pmMKE - ORD
2 stops29h 17mMultiple Airlines
Wed 12/36:48 amORD - MKE
1 stop26h 51mMultiple Airlines
Deal found 10/29$272
This Southwest deal was found by Cheapflights users on 10/30. 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 11/266:30 pmMKE - MDW
1 stop3h 15mSouthwest
Thu 11/278:20 amMDW - MKE
1 stop3h 55mSouthwest
Deal found 10/30$307
This Southwest deal was found by Cheapflights users on 10/30. 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 11/266:30 pmMKE - MDW
1 stop3h 15mSouthwest
Fri 11/289:30 amMDW - MKE
2 stops7h 55mSouthwest
Deal found 10/30$312
This Southwest deal was found by Cheapflights users on 10/28. 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 11/215:50 amMKE - MDW
1 stop4h 05mSouthwest
Fri 11/287:00 pmMDW - MKE
1 stop4h 30mSouthwest
Deal found 10/28$327

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 October 30, 2025.
Use the filters below to find and compare flights from Milwaukee to Chicago that are best for you.

Fly from

Milwaukee

Fly to

Chicago

Route

Depart

Return

Price

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sat 11/29

5:00 am-6:11 am

Nonstop1h 11m

Chicago O'Hare Intl

Sat 12/6

9:49 am-10:43 am

Nonstop0h 54m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 12/25

5:00 am-6:22 am

Nonstop1h 22m

Chicago O'Hare Intl

Tue 12/30

9:07 pm-10:13 pm

Nonstop1h 06m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 11/28

10:53 am-12:04 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sun 11/30

8:51 pm-9:59 pm

Nonstop1h 08m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 12/3

8:06 am-9:22 am

Nonstop1h 16m

Chicago O'Hare Intl

Thu 12/11

5:03 pm-5:58 pm

Nonstop0h 55m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 11/28

3:28 pm-4:40 pm

Nonstop1h 12m

Chicago O'Hare Intl

Fri 12/5

10:00 pm-11:05 pm

Nonstop1h 05m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 3/9

3:15 pm-4:21 pm

Nonstop1h 06m

Chicago O'Hare Intl

Thu 3/19

9:25 am-10:30 am

Nonstop1h 05m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sun 11/23

5:00 am-6:11 am

Nonstop1h 11m

Chicago O'Hare Intl

Fri 11/28

6:30 pm-7:44 pm

Nonstop1h 14m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 11/13

5:00 am-6:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Mon 11/17

5:34 pm-6:27 pm

Nonstop0h 53m

$209

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 11/27

12:35 pm-11:06 pm

1 stop10h 31m

Chicago O'Hare Intl

Thu 12/4

1:52 pm-9:39 am

2 stops19h 47m

$240

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sun 12/7

6:09 pm-2:21 pm

1 stop20h 12m

Chicago O'Hare Intl

Fri 12/12

7:20 am-5:09 pm

1 stop9h 49m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 37 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-Chicago flight deals on Cheapflights vs. eDreams >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 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 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, November is the cheapest month in which you can book a flight from Milwaukee to Chicago (average of $173). Flying from Milwaukee to Chicago in July is currently the most expensive (average of $238). 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 October 30, 2025.

It’s optimal to fly from Milwaukee to Chicago in the afternoon. By choosing this option you can save up to 27% 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 October 26, 2025.

Travelers seeking maximum savings on their Milwaukee to Chicago flight should consider departing on Sunday 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.

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 October 30, 2025.
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
7.2
Good
11,034 reviews

Food

6.4

Crew

8.0

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

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
7.2
Good
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Food

6.4

Crew

8.0

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

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 24 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 $179, American Airlines can have you in Chicago from Milwaukee in 1h 11m. The distance between Milwaukee and Chicago is about 67 mi. This flight may include one or multiple stops.

  • 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. American Airlines is priced at 39% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Milwaukee to Chicago one-way?

    The cheapest airlines for a one-way flight from Milwaukee to Chicago are Frontier ($106), Southwest ($110), and Spirit Airlines ($115).

  • 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 Avianca (79%), Copa Airlines (76%) or United Airlines (75%) 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 $871, our data indicates the cheapest price to be $107. The most popular route (Milwaukee-Mitchell - Chicago O'Hare Intl), is priced around $179.

  • 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, November is the cheapest month in which you can book a flight from Milwaukee to Chicago (average of $173). Flying from Milwaukee to Chicago in July is currently the most expensive (average of $238). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Milwaukee to Chicago

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$264FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$309FlexibilityNo cancel feeOn-time69%

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