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$49+ Cheap flights from Wisconsin 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 1/27. 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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Find flight deals from Wisconsin to Chicago

Cheapest flights from Wisconsin to Chicago
Explore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:31 amMSP - ORD
Nonstop1h 45mFrontier
Thu 12/117:00 amORD - MSP
1 stop11h 12mFrontier
Deal found 10/29$75
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:54 amMSP - ORD
Nonstop1h 45mSun Country Air
Thu 11/279:20 amORD - MSP
Nonstop1h 42mSun Country Air
Deal found 10/30$78
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/149:06 amMSP - ORD
Nonstop1h 45mMultiple Airlines
Mon 12/156:00 amORD - MSP
Nonstop1h 36mMultiple Airlines
Deal found 10/29$80
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:31 amMSP - ORD
Nonstop1h 45mFrontier
Mon 12/87:00 amORD - MSP
1 stop17h 02mFrontier
Deal found 10/30$82
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/149:06 amMSP - ORD
Nonstop1h 45mMultiple Airlines
Fri 12/2612:26 pmORD - MSP
Nonstop1h 36mMultiple Airlines
Deal found 10/30$87
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/238:41 amMSP - ORD
Nonstop1h 35mFrontier
Wed 11/266:13 amORD - MSP
Nonstop1h 33mFrontier
Deal found 10/30$88
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:57 pmMSP - ORD
Nonstop1h 45mMultiple Airlines
Tue 12/306:44 pmORD - MSP
Nonstop1h 39mMultiple Airlines
Deal found 10/30$90
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:31 amMSP - ORD
Nonstop1h 45mMultiple Airlines
Sun 12/149:40 pmORD - MSP
Nonstop1h 42mMultiple Airlines
Deal found 10/30$93
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:24 amMSP - MDW
Nonstop1h 55mDelta
Wed 12/107:02 pmMDW - MSP
Nonstop1h 43mDelta
Deal found 10/28$97
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:30 amMSP - MDW
1 stop5h 55mSouthwest
Tue 12/911:25 amMDW - MSP
Nonstop1h 30mSouthwest
Deal found 10/29$107
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1011:30 amMSP - MDW
1 stop7h 09mFrontier
Mon 11/1712:30 pmMDW - MSP
1 stop11h 44mFrontier
Deal found 10/27$110
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.
Wed 12/103:50 pmMSP - MDW
1 stop4h 55mSouthwest
Mon 12/155:15 pmMDW - MSP
1 stop4h 30mSouthwest
Deal found 10/28$117

Cheap flight deals from Wisconsin to Chicago

Keep the following information in mind while searching for Wisconsin to Chicago flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$75
(Frontier)

One-way from

$49
(Delta)

Popular in

November

Cheapest in

June

Average price

$222

Good round-trip deal

$293 or less

Good one-way deal

$170 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 Wisconsin to Chicago (CHI)
Search Deals
One-way flight from Wisconsin to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Wisconsin to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Wisconsin to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 Wisconsin to Chicago that are best for you.

Fly from

Wisconsin

Fly to

Chicago

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/10

7:24 am-9:19 am

Nonstop1h 55m

Chicago Midway

Wed 12/10

1:50 pm-3:30 pm

Nonstop1h 40m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 12/8

4:54 pm-6:35 pm

Nonstop1h 41m

Chicago O'Hare Intl

Tue 12/9

6:10 pm-7:40 pm

Nonstop1h 30m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 12/8

8:00 pm-9:40 pm

Nonstop1h 40m

Chicago O'Hare Intl

Mon 12/15

6:00 am-7:37 am

Nonstop1h 37m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/17

5:45 am-12:35 pm

2 stops6h 50m

Chicago Midway

Wed 12/31

8:45 pm-10:15 pm

Nonstop1h 30m

$112

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/3

4:30 pm-6:18 pm

Nonstop1h 48m

Chicago Midway

Fri 12/5

1:50 pm-3:30 pm

Nonstop1h 40m

$120

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 12/12

7:24 am-9:19 am

Nonstop1h 55m

Chicago Midway

Mon 12/15

9:59 am-11:42 am

Nonstop1h 43m

$120

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 12/6

1:40 pm-3:17 pm

Nonstop1h 37m

Chicago O'Hare Intl

Mon 12/8

8:40 pm-10:15 pm

Nonstop1h 35m

$120

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 11/17

11:29 am-12:11 am

1 stop12h 42m

Chicago O'Hare Intl

Tue 11/18

6:05 pm-9:24 pm

1 stop27h 19m

$128

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 12/5

7:15 am-9:00 am

Nonstop1h 45m

Chicago Midway

Mon 12/8

5:15 pm-9:45 pm

1 stop4h 30m

$130

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 11/17

9:00 am-10:45 am

Nonstop1h 45m

Chicago O'Hare Intl

Tue 11/18

6:05 pm-9:24 pm

1 stop27h 19m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Wisconsin 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 Wisconsin to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $155). Flying from Wisconsin to Chicago in January is currently the most expensive (average of $198). 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 WI to CHI?

Find hourly flight availability from Wisconsin 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.

One of the essential ways to save on airfare from Wisconsin to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 24% on airfare.

What is the cheapest day to fly from Wisconsin to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Chicago flight should consider departing on Thursday mornings 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.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Wisconsin to Chicago?

    A quick flight from Wisconsin to Chicago can take about 1h 41m. Delta provides one of the quickest options available for as low as $97. Wisconsin and Chicago are separated by a distance of 333 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $49 on Delta. Other airlines that offer cheap prices include Southwest from $49 and United Airlines from $49 one-way.

  • What are the most popular routes from Wisconsin to Chicago?

    The most popular route from Wisconsin to Chicago is Minneapolis St Paul - Chicago O'Hare Intl. You may also consider Minneapolis St Paul - Chicago Midway or Dubuque - Chicago O'Hare Intl.

  • What are the most reliable airlines from Wisconsin to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Wisconsin to Chicago on time: Avianca (79%), Copa Airlines (76%), United Airlines (75%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $871, our data indicates the cheapest price to be $107. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $64.

  • Can I find deals for flights from Wisconsin to Chicago that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Chicago.

  • Can I find deals for business class flights from Wisconsin to Chicago?

    Yes. Cheapflights offers flight deals from Wisconsin 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 Wisconsin to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $155). Flying from Wisconsin to Chicago in January is currently the most expensive (average of $198). 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 Wisconsin to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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San Francisco to Midway flights
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Boston to Midway flights

Top 2 airlines flying from Wisconsin to Chicago

Discover the top 2 airlines that operate flights from Wisconsin 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
United AirlinesCheapest$179Average$276FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$306FlexibilityNo cancel feeOn-time71%

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