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$64+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
1 adult, Economy
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Cheap 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 enero 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/197:25 am
ORD
-
MSP
Nonstop1h 30m
United Airlines
mié. 2/258:05 am
MSP
-
ORD
Nonstop1h 41m
United Airlines
Deal found 1/27$134
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/1912:25 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
mar. 2/247:20 am
MSP
-
MDW
Nonstop1h 55m
Southwest
Deal found 1/27$134
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/136:40 pm
ORD
-
MSP
Nonstop1h 43m
Sun Country Air
sáb. 3/147:18 pm
MSP
-
ORD
Nonstop1h 32m
Sun Country Air
Deal found 1/28$137
This Sun Country Air deal was found by Cheapflights users on 1/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/237:13 pm
ORD
-
MSP
Nonstop1h 44m
Sun Country Air
lun. 5/115:30 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Deal found 1/26$138
This Trip.com deal was found by Cheapflights users on 1/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/237:13 pm
ORD
-
MSP
Nonstop1h 44m
Sun Country Air
lun. 4/277:36 am
MSP
-
ORD
Nonstop1h 39m
Sun Country Air
Deal found 1/27$143
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/132:15 pm
ORD
-
MSP
Nonstop1h 35m
United Airlines
mié. 3/189:55 am
MSP
-
ORD
Nonstop1h 41m
United Airlines
Deal found 1/28$144
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/148:06 pm
ORD
-
MSP
Nonstop1h 42m
Sun Country Air
vie. 5/155:30 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Deal found 1/27$148
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/54:35 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
mar. 3/108:45 am
MSP
-
MDW
2 stops7h 55m
Southwest
Deal found 1/27$149
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/2510:23 pm
ORD
-
MSP
Nonstop1h 33m
American Airlines
mié. 3/46:35 am
MSP
-
ORD
Nonstop1h 45m
American Airlines
Deal found 1/27$152
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/267:55 am
MDW
-
MSP
1 stop3h 30m
Southwest
mar. 3/36:50 am
MSP
-
MDW
1 stop6h 35m
Southwest
Deal found 1/27$154
This Trip.com deal was found by Cheapflights users on 1/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/237:13 pm
ORD
-
MSP
Nonstop1h 42m
Multiple Airlines
lun. 4/273:40 pm
MSP
-
ORD
1 stop9h 12m
Multiple Airlines
Deal found 1/27$155
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/188:40 am
ORD
-
MSP
Nonstop1h 30m
United Airlines
mar. 2/246:00 am
MSP
-
ORD
Nonstop1h 41m
United Airlines
Deal found 1/27$157

Find flight deals from Chicago to Wisconsin

Keep the following information in mind while searching for Chicago to Wisconsin flight deals. Data was last updated enero 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$134
(United Airlines)

One-way from

$64
(Southwest)

Good round-trip deal

$438 or less

Good one-way deal

$150 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
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 enero 29, 2026.
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

mié. 3/11

8:10 pm-9:46 pm

Nonstop1h 36m

Minneapolis St Paul

lun. 3/16

9:55 am-11:36 am

Nonstop1h 41m

$134

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

mié. 4/8

6:15 am-7:57 am

Nonstop1h 42m

Minneapolis St Paul

sáb. 4/11

6:10 pm-7:49 pm

Nonstop1h 39m

$134

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 2/19

7:25 am-8:55 am

Nonstop1h 30m

Minneapolis St Paul

mié. 2/25

8:05 am-9:46 am

Nonstop1h 41m

$134

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

mié. 3/11

7:20 pm-9:00 pm

Nonstop1h 40m

Minneapolis St Paul

lun. 3/16

5:07 pm-6:40 pm

Nonstop1h 33m

$134

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

sáb. 2/21

3:56 pm-5:28 pm

Nonstop1h 32m

Minneapolis St Paul

mar. 2/24

9:51 am-11:32 am

Nonstop1h 41m

$134

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

mié. 4/8

2:05 pm-3:44 pm

Nonstop1h 39m

Minneapolis St Paul

sáb. 4/11

7:00 am-8:50 am

Nonstop1h 50m

$134

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

vie. 4/24

7:35 pm-9:19 pm

Nonstop1h 44m

Minneapolis St Paul

lun. 5/11

5:30 pm-7:06 pm

Nonstop1h 36m

$138

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 4/23

7:13 pm-8:57 pm

Nonstop1h 44m

Minneapolis St Paul

lun. 5/11

5:30 pm-7:06 pm

Nonstop1h 36m

$138

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

jue. 2/19

8:50 pm-10:20 pm

Nonstop1h 30m

Minneapolis St Paul

mar. 2/24

7:45 am-2:20 pm

1 stop6h 35m

$144

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

mié. 3/11

11:05 am-12:35 pm

Nonstop1h 30m

Minneapolis St Paul

lun. 3/16

5:30 pm-11:00 pm

1 stop5h 30m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 enero 29, 2026.

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 afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 15% 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 January 24, 2026.

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

Weekly flight availability from Chicago to Wisconsin

Explore weekly flight availability from Chicago to Wisconsin. 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 enero 29, 2026.

The most flights from CHI to USWI are scheduled on a Wednesday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).

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 enero 29, 2026.
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
9,215 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 $134, United Airlines can have you in Wisconsin from Chicago in 1h 36m. There are 333 mi between Chicago and Wisconsin. Generally, flights for this route are nonstop.

  • 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: Republic Airways (73%), Air Canada (63%), Lufthansa( 63%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $169 for a flight from Chicago to Wisconsin. The cheapest flight overall is $98 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $97.

  • 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.

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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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$334FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$320FlexibilityNo cancel feeOn-time69%

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