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$93+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$93
(Southwest)

Popular in

November

Cheapest in

June

Average price

$239

Good round-trip deal

$323 or less

Good one-way deal

$171 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 ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. 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 10/105:25 amMKE - ORD
Nonstop1h 04mAmerican Airlines
Tue 10/1411:00 pmORD - MKE
Nonstop0h 56mAmerican Airlines
Deal found 9/13$179
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/292:05 pmMKE - ORD
Nonstop1h 09mAmerican Airlines
Wed 11/56:07 pmORD - MKE
Nonstop1h 07mAmerican Airlines
Deal found 9/14$180
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/308:43 amMKE - ORD
Nonstop1h 05mAmerican Airlines
Sat 10/45:55 pmORD - MKE
Nonstop0h 53mAmerican Airlines
Deal found 9/15$189
This United Airlines deal was found by Cheapflights users on 9/15. 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 9/255:00 amMKE - ORD
Nonstop1h 10mUnited Airlines
Tue 9/309:05 amORD - MKE
Nonstop1h 06mUnited Airlines
Deal found 9/15$199
This Southwest deal was found by Cheapflights users on 9/13. 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 10/284:05 pmMKE - MDW
1 stop6h 00mSouthwest
Fri 11/147:00 pmMDW - MKE
1 stop4h 30mSouthwest
Deal found 9/13$219
This Southwest deal was found by Cheapflights users on 9/12. 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 10/107:30 pmMKE - MDW
1 stop3h 45mSouthwest
Sun 10/127:20 amMDW - MKE
1 stop4h 30mSouthwest
Deal found 9/12$225
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/115:45 pmMKE - ORD
Nonstop1h 10mUnited Airlines
Mon 10/138:50 pmORD - MKE
Nonstop1h 06mUnited Airlines
Deal found 9/13$239
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/73:42 pmMKE - ORD
Nonstop1h 12mAmerican Airlines
Fri 12/199:05 amORD - MKE
Nonstop1h 08mAmerican Airlines
Deal found 9/15$247
This Southwest deal was found by Cheapflights users on 9/13. 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 10/107:30 pmMKE - MDW
1 stop3h 45mSouthwest
Tue 10/145:55 pmMDW - MKE
1 stop4h 05mSouthwest
Deal found 9/13$258
This United Airlines deal was found by Cheapflights users on 9/14. 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 9/256:00 amMKE - ORD
Nonstop1h 10mUnited Airlines
Sun 9/289:05 amORD - MKE
Nonstop1h 06mUnited Airlines
Deal found 9/14$259
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/138:16 pmMKE - ORD
Nonstop1h 14mAmerican Airlines
Mon 10/207:25 pmORD - MKE
Nonstop1h 00mAmerican Airlines
Deal found 9/13$261
This Southwest deal was found by Cheapflights users on 9/15. 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 11/255:50 amMKE - MDW
1 stop4h 15mSouthwest
Fri 11/289:30 amMDW - MKE
2 stops7h 55mSouthwest
Deal found 9/15$273

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 September 15, 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

Fri 10/10

5:25 am-6:29 am

Nonstop1h 04m

Chicago O'Hare Intl

Tue 10/14

11:00 pm-11:56 pm

Nonstop0h 56m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sat 10/11

6:40 pm-7:50 pm

Nonstop1h 10m

Chicago O'Hare Intl

Sat 10/18

10:20 am-11:26 am

Nonstop1h 06m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 10/10

4:59 pm-6:10 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sun 10/12

9:27 am-10:33 am

Nonstop1h 06m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 10/16

6:00 am-7:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Mon 10/20

8:50 pm-9:56 pm

Nonstop1h 06m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 10/10

5:25 am-6:29 am

Nonstop1h 04m

Chicago O'Hare Intl

Mon 10/13

6:36 pm-7:46 pm

Nonstop1h 10m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sun 12/7

5:35 pm-6:46 pm

Nonstop1h 11m

Chicago O'Hare Intl

Thu 12/18

6:40 pm-7:55 pm

Nonstop1h 15m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 11/11

5:00 am-6:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Sat 11/22

4:49 pm-5:43 pm

Nonstop0h 54m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 10/9

12:05 pm-1:15 pm

Nonstop1h 10m

Chicago O'Hare Intl

Sun 10/12

8:50 pm-9:56 pm

Nonstop1h 06m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sun 10/12

8:26 am-9:30 am

Nonstop1h 04m

Chicago O'Hare Intl

Sun 10/19

9:27 am-10:33 am

Nonstop1h 06m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 10/10

4:59 pm-6:10 pm

Nonstop1h 11m

Chicago O'Hare Intl

Wed 10/15

12:53 pm-1:48 pm

Nonstop0h 55m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 38 results
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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 September 15, 2025.

It’s optimal to fly from Milwaukee to Chicago in the morning. By choosing this option you can save up to 36% 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 September 7, 2025.

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

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 September 15, 2025.

The most flights from MKE to CHI are scheduled on a Thursday (52 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (31 on average).

How much does it cost to fly round-trip from Milwaukee to Chicago?

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 September 15, 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
10,000 reviews

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 $179, American Airlines can have you in Chicago from Milwaukee in 1h 04m. 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 ($100), Southwest ($110), and Sun Country Air ($121).

  • 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 Copa Airlines (66%), Avianca (66%) or United Airlines (64%) 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 $877, our data indicates the cheapest price to be $108. 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
Chesterton

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Alternative routes for Milwaukee to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$264FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$309FlexibilityNo cancel feeOn-time69%

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