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$109+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$179
(United Airlines)

One-way from

$109
(Mytrip)

Popular in

November

Cheapest in

June

Good round-trip deal

$322 or less

Good one-way deal

$191 or less
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. 13% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($22 potential savings vs. average RT price).
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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 July 31, 2025.

This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/217:00 amMKE - ORD
Nonstop1h 10mUnited Airlines
Mon 8/259:35 pmORD - MKE
Nonstop1h 06mUnited Airlines
Deal found 7/30$179
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/147:49 pmMKE - ORD
Nonstop1h 04mAmerican Airlines
Sun 8/178:35 amORD - MKE
Nonstop0h 53mAmerican Airlines
Deal found 7/31$189
This Mytrip deal was found by Cheapflights users on 7/31. 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 8/286:00 amMKE - ORD
1 stop16h 22mSpirit Airlines
Fri 8/296:56 amORD - MKE
1 stop16h 10mSpirit Airlines
Deal found 7/31$246

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 July 31, 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

Thu 8/21

7:00 am-8:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Mon 8/25

9:35 pm-10:41 pm

Nonstop1h 06m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 8/14

7:49 pm-8:53 pm

Nonstop1h 04m

Chicago O'Hare Intl

Sun 8/17

8:35 am-9:28 am

Nonstop0h 53m

$189

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 8/28

6:00 am-10:22 pm

1 stop16h 22m

Chicago O'Hare Intl

Fri 8/29

6:56 am-11:06 pm

1 stop16h 10m

$246

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 8/27

6:30 am-11:59 pm

1 stop17h 29m

Chicago O'Hare Intl

Wed 9/3

1:01 pm-12:02 am

1 stop11h 01m

$478

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 9/4

12:53 pm-9:58 pm

1 stop9h 05m

$109

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 9/26

6:32 pm-9:10 am

1 stop14h 38m

$195

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sun 9/14

4:33 pm-5:45 pm

Nonstop1h 12m

$203

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 8/28

3:44 pm-4:54 pm

Nonstop1h 10m

$219

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 9/30

6:27 am-4:49 pm

1 stop10h 22m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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, August is the cheapest month in which you can book a flight from Milwaukee to Chicago (average of $245). Flying from Milwaukee to Chicago in March is currently the most expensive (average of $321). 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 July 31, 2025.

It’s optimal to fly from Milwaukee to Chicago in the morning. By choosing this option you can save up to 42% 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 July 31, 2025.

The most flights from MKE to CHI are scheduled on a Thursday (51 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (34 on average).

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 July 31, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta, and United 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Spirit Airlines
6.3
Okay
8,049 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 41 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.

  • 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. Other airlines that can offer you cheap pricing are American Airlines, from $189, and Spirit Airlines, from $246. United Airlines is priced at 41% 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 Spirit Airlines ($109), Delta ($195), and American Airlines ($203).

  • 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 (75%), Copa Airlines (73%) or Air Canada (72%) 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 $1,014, our data indicates the cheapest price to be $98. 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, August is the cheapest month in which you can book a flight from Milwaukee to Chicago (average of $245). Flying from Milwaukee to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Valparaiso
Chesterton

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$278FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$309FlexibilityNo cancel feeOn-time69%

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