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$125+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$125
(Mytrip)

Popular in

November

Cheapest in

March

Average price

$303

Good round-trip deal

$331 or less

Good one-way deal

$175 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. 3% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

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.
Sat 6/215:18 pmMKE - ORD
Nonstop1h 09mAmerican Airlines
Sat 6/2810:25 pmORD - MKE
Nonstop0h 55mAmerican Airlines
Deal found 4/30$179
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2712:22 pmMKE - ORD
1 stop7h 41mSpirit Airlines
Tue 6/39:02 pmORD - MKE
1 stop21h 57mSpirit Airlines
Deal found 4/29$227
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:00 amMKE - ORD
Nonstop1h 10mUnited Airlines
Mon 10/208:50 pmORD - MKE
Nonstop1h 06mUnited Airlines
Deal found 4/29$239
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/126:11 pmMKE - ORD
1 stop23h 04mMultiple Airlines
Thu 6/1910:19 amORD - MKE
1 stop21h 47mMultiple Airlines
Deal found 4/30$307
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/152:36 pmMKE - ORD
1 stop9h 23mAlaska Airlines
Mon 10/209:00 pmORD - MKE
1 stop16h 45mAlaska Airlines
Deal found 4/29$532
This KAYAK deal was found by Cheapflights users on 4/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/96:38 amMKE - ORD
1 stop12h 54mDelta
Fri 6/139:00 amORD - MKE
2 stops12h 30mDelta
Deal found 4/29$688

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 1, 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 6/21

5:18 pm-6:27 pm

Nonstop1h 09m

Chicago O'Hare Intl

Sat 6/28

10:25 pm-11:20 pm

Nonstop0h 55m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 5/27

12:22 pm-8:03 pm

1 stop7h 41m

Chicago O'Hare Intl

Tue 6/3

9:02 pm-6:59 pm

1 stop21h 57m

$227

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 5/13

5:47 pm-6:55 pm

Nonstop1h 08m

Chicago O'Hare Intl

Wed 5/21

9:13 pm-10:15 pm

Nonstop1h 02m

$244

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 6/12

6:11 pm-5:15 pm

1 stop23h 04m

Chicago O'Hare Intl

Thu 6/19

10:19 am-8:06 am

1 stop21h 47m

$307

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 5/13

3:06 pm-6:05 am

1 stop14h 59m

Chicago O'Hare Intl

Wed 5/21

10:00 am-11:59 pm

1 stop13h 59m

$637

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 6/9

6:38 am-7:32 pm

1 stop12h 54m

Chicago O'Hare Intl

Fri 6/13

9:00 am-9:30 pm

2 stops12h 30m

$688

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 5/21

7:54 pm-10:55 am

1 stop15h 01m

$125

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 5/28

6:18 am-5:02 pm

1 stop10h 44m

$197

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 5/21

6:30 am-7:30 am

Nonstop1h 00m

$204

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 5/27

8:35 am-9:40 am

Nonstop1h 05m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 11 results
1
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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*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 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, 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 May 1, 2025.

It’s optimal to fly from Milwaukee to Chicago in the morning. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the afternoon.

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 1, 2025.

The most flights from MKE to CHI are scheduled on a Wednesday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 1, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta and United Airlines from Milwaukee to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
7,963 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 26 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 Spirit Airlines, from $227, and United Airlines, from $244. American Airlines is priced at 47% 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 ($125), Alaska Airlines ($197), and American Airlines ($204).

  • 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 Envoy Air (100%), Copa Airlines (85%) or Avianca (78%) 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 $901, our data indicates the cheapest price to be $118. 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 Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$291FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$309FlexibilityNo cancel feeOn-time69%

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