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$58+ Cheap flights from Chicago (CHI) to Wisconsin

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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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Find flight deals from Chicago to Wisconsin

Cheapest flights from Chicago to Wisconsin
Explore the most affordable flight options available from Chicago to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 29, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/1711:42 amORD - MSP
Nonstop1h 42mSun Country Air
lun. 11/248:54 amMSP - ORD
Nonstop1h 45mSun Country Air
Deal found 10/27$78
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:00 amORD - MSP
Nonstop1h 36mMultiple Airlines
dom. 12/149:06 amMSP - ORD
Nonstop1h 45mMultiple Airlines
Deal found 10/27$80
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/86:00 amORD - MSP
Nonstop1h 36mMultiple Airlines
vie. 12/129:06 amMSP - ORD
Nonstop1h 45mMultiple Airlines
Deal found 10/29$81
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.
jue. 12/47:00 amORD - MSP
1 stop11h 12mFrontier
lun. 12/88:31 amMSP - ORD
Nonstop1h 45mFrontier
Deal found 10/27$82
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/227:38 pmORD - MSP
Nonstop1h 36mFrontier
lun. 12/2910:09 pmMSP - ORD
Nonstop1h 45mFrontier
Deal found 10/28$83
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/2612:26 pmORD - MSP
Nonstop1h 36mFrontier
lun. 12/2910:09 pmMSP - ORD
Nonstop1h 45mFrontier
Deal found 10/28$84
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/188:08 pmORD - MSP
Nonstop1h 39mSun Country Air
dom. 12/215:12 pmMSP - ORD
Nonstop1h 38mSun Country Air
Deal found 10/27$85
This Priceline deal was found by Cheapflights users on 10/26. 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.
jue. 11/207:32 pmORD - MSP
Nonstop1h 42mMultiple Airlines
dom. 11/238:41 amMSP - ORD
Nonstop1h 35mMultiple Airlines
Deal found 10/26$90
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/87:00 amORD - MSP
1 stop17h 02mFrontier
vie. 12/128:31 amMSP - ORD
Nonstop1h 45mFrontier
Deal found 10/29$91
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/2612:26 pmORD - MSP
Nonstop1h 36mMultiple Airlines
lun. 12/295:00 pmMSP - ORD
Nonstop1h 38mMultiple Airlines
Deal found 10/27$92
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/227:38 pmORD - MSP
Nonstop1h 36mMultiple Airlines
dom. 12/285:30 amMSP - ORD
Nonstop1h 49mMultiple Airlines
Deal found 10/28$93
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/2411:03 amORD - MSP
Nonstop1h 39mMultiple Airlines
vie. 12/262:57 pmMSP - ORD
Nonstop1h 45mMultiple Airlines
Deal found 10/27$94

Cheap flight deals from Chicago to Wisconsin

Keep the following information in mind while searching for Chicago to Wisconsin flight deals. Data was last updated octubre 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$78
(Cheapflightsfares)

One-way from

$58
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$304

Good round-trip deal

$179 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for Chicago (CHI)-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Milwaukee-Mitchell flights.
Search Deals
From Chicago (CHI) to Wisconsin
Search Deals
One-way flight from Chicago (CHI) to Wisconsin
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($25 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 Chicago (CHI) to Wisconsin.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Wisconsin.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Wisconsin 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 octubre 29, 2025.
Use the filters below to find and compare flights from Chicago to Wisconsin that are best for you.

Fly from

Chicago

Fly to

Wisconsin

Route

Depart

Return

Price

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

lun. 12/22

7:38 pm-9:14 pm

Nonstop1h 36m

Minneapolis St Paul

dom. 12/28

5:30 am-7:19 am

Nonstop1h 49m

$93

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

lun. 12/8

8:50 am-10:24 am

Nonstop1h 34m

Minneapolis St Paul

mar. 12/9

3:16 pm-4:57 pm

Nonstop1h 41m

$97

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

mié. 1/14

1:49 pm-3:37 pm

Nonstop1h 48m

Minneapolis St Paul

jue. 1/15

7:05 am-9:08 am

Nonstop2h 03m

$97

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

mié. 2/25

2:00 pm-3:40 pm

Nonstop1h 40m

Minneapolis St Paul

jue. 2/26

11:30 am-1:08 pm

Nonstop1h 38m

$97

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

dom. 1/18

2:17 pm-3:48 pm

Nonstop1h 31m

Minneapolis St Paul

mié. 1/21

8:00 am-9:45 am

Nonstop1h 45m

$99

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 11/27

8:50 am-10:25 am

Nonstop1h 35m

Minneapolis St Paul

jue. 12/4

8:00 am-9:41 am

Nonstop1h 41m

$109

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

mié. 1/14

1:25 pm-8:35 pm

2 stops7h 10m

Minneapolis St Paul

jue. 1/15

12:00 pm-1:35 pm

Nonstop1h 35m

$112

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

vie. 11/21

10:24 am-12:06 pm

Nonstop1h 42m

Minneapolis St Paul

lun. 11/24

8:54 am-10:39 am

Nonstop1h 45m

$118

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

jue. 11/27

8:15 am-9:50 am

Nonstop1h 35m

Minneapolis St Paul

jue. 12/4

5:30 am-11:25 am

1 stop5h 55m

$119

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 12/4

8:50 am-10:24 am

Nonstop1h 34m

Minneapolis St Paul

dom. 12/7

6:10 pm-7:55 pm

Nonstop1h 45m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $178). Flying from Chicago to Wisconsin in March is currently the most expensive (average of $268). 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 CHI to WI?

Find hourly flight availability from Chicago to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 29, 2025.

One of the essential ways to save on airfare from Chicago to Wisconsin is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 19% on airfare.

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

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

Travelers seeking maximum savings on their Chicago to Wisconsin flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated octubre 29, 2025.
See what other customers who have flown with United Airlines and American Airlines from Chicago to Wisconsin have to say. 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.
United Airlines
7.4
Good
8,999 reviews

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,999 reviews
United Airlines
7.4
Good
8,999 reviews

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,032 reviews
United Airlines
7.4
Good
8,999 reviews

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from Chicago to Wisconsin. 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 Chicago to Wisconsin?

    For as low as $99, Delta can have you in Wisconsin from Chicago in 1h 31m. There are 333 mi between Chicago and Wisconsin. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $59 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $59 and $106, respectively.

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

    Most travelers choose Chicago O'Hare Intl - Minneapolis St Paul, Chicago Midway - Minneapolis St Paul or Chicago O'Hare Intl - Duluth Intl when deciding on the best route from Chicago to Wisconsin.

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

    Before booking your flight to Wisconsin from Chicago, check out the most reliable airlines to get you to your destination on time: Emirates (80%), ANA (78%), Copa Airlines( 78%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $179 for a flight from Chicago to Wisconsin. The cheapest flight overall is $179 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $63.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $178). Flying from Chicago to Wisconsin in March is currently the most expensive (average of $268). 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

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Alternative routes for Chicago to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Wisconsin

Discover the top 2 airlines that operate flights from Chicago to Wisconsin. 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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$307FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$290FlexibilityNo cancel feeOn-time69%

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