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$59+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
dic. 24 — dic. 311
mar. 12/24
mar. 12/31
1 adult, Economy
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Cheap flight deals from Wisconsin to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Wisconsin (USWI) 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 diciembre 19, 2024.

Round-trip from

$116
(Cheapflightsfares)

One-way from

$59
(Sun Country Air)
From Wisconsin to Chicago (CHI)
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One-way flight from Wisconsin to Chicago (CHI)
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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 diciembre 19, 2024.

This Sun Country Air deal was found by Cheapflights users on 12/17. 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.
mar. 12/314:00 pmMSP - ORD
Nonstop1h 38mSun Country Air
lun. 1/67:00 pmORD - MSP
Nonstop1h 31mSun Country Air
Deal found 12/17$128
This FlightHub deal was found by Cheapflights users on 12/18. 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.
mar. 12/314:00 pmMSP - ORD
Nonstop1h 38mMultiple Airlines
vie. 1/36:00 amORD - MSP
1 stop17h 56mMultiple Airlines
Deal found 12/18$144
This American Airlines deal was found by Cheapflights users on 12/17. 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.
mar. 12/316:15 amMSP - ORD
Nonstop1h 55mAmerican Airlines
mar. 1/288:52 pmORD - MSP
Nonstop1h 36mAmerican Airlines
Deal found 12/17$178
This Booking.com deal was found by Cheapflights users on 12/17. 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.
mié. 12/255:45 amMSP - ORD
1 stop18h 01mFrontier
mié. 1/16:00 amORD - MSP
1 stop17h 56mFrontier
Deal found 12/17$208
This Southwest deal was found by Cheapflights users on 12/17. 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.
mar. 12/316:00 amMSP - MDW
Nonstop1h 45mSouthwest
mié. 1/110:55 amMDW - MSP
Nonstop1h 30mSouthwest
Deal found 12/17$220
This United Airlines deal was found by Cheapflights users on 12/17. 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. 12/256:00 amMSP - ORD
Nonstop1h 42mUnited Airlines
mié. 1/18:20 pmORD - MSP
Nonstop1h 35mUnited Airlines
Deal found 12/17$225
This Delta deal was found by Cheapflights users on 12/17. 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.
mar. 12/318:55 pmMSP - ORD
Nonstop1h 57mDelta
mar. 1/710:30 amORD - MSP
1 stop7h 10mDelta
Deal found 12/17$230
This United Airlines deal was found by Cheapflights users on 12/18. 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. 12/267:45 amDLH - ORD
Nonstop2h 09mUnited Airlines
jue. 1/28:13 pmORD - DLH
Nonstop1h 47mUnited Airlines
Deal found 12/18$269
This Delta deal was found by Cheapflights users on 12/18. 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.
mar. 12/313:27 pmMSP - MDW
Nonstop1h 44mDelta
jue. 1/211:48 amMDW - MSP
Nonstop1h 43mDelta
Deal found 12/18$304
This CheapOair deal was found by Cheapflights users on 12/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/1911:27 amMSP - MDW
1 stop8h 15mFrontier
lun. 1/207:15 amMDW - MSP
1 stop15h 53mFrontier
Deal found 12/17$308
This Mytrip deal was found by Cheapflights users on 12/19. 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.
mar. 12/314:41 pmMSP - ORD
2 stops15h 56mSpirit Airlines
dom. 1/51:24 pmORD - MSP
2 stops22h 53mSpirit Airlines
Deal found 12/19$317
This Southwest deal was found by Cheapflights users on 12/18. 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.
mar. 12/312:45 pmMSP - ORD
1 stop7h 15mSouthwest
vie. 1/311:25 amORD - MSP
1 stop4h 25mSouthwest
Deal found 12/18$350

Find flights from Wisconsin to Chicago within your budget

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 diciembre 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

jue. 4/10

4:27 pm-6:06 pm

Nonstop1h 39m

Chicago O'Hare Intl

dom. 4/13

9:13 pm-10:57 pm

Nonstop1h 44m

$116

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

mar. 1/7

6:00 am-12:13 am

1 stop18h 13m

Chicago Midway

mar. 1/14

8:15 am-11:04 pm

1 stop14h 49m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

mar. 1/7

6:58 am-8:40 am

Nonstop1h 42m

Chicago O'Hare Intl

mar. 1/14

8:52 pm-10:28 pm

Nonstop1h 36m

$137

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

mar. 12/31

4:00 pm-5:38 pm

Nonstop1h 38m

Chicago O'Hare Intl

vie. 1/3

6:00 am-11:56 pm

1 stop17h 56m

$144

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

dom. 1/12

6:00 am-12:35 am

1 stop18h 35m

Chicago O'Hare Intl

vie. 1/24

8:46 pm-12:02 pm

1 stop15h 16m

$150

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

sáb. 2/8

1:56 pm-3:30 pm

Nonstop1h 34m

Chicago O'Hare Intl

mié. 2/12

6:15 am-8:01 am

Nonstop1h 46m

$152

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

vie. 1/24

5:30 am-7:05 am

Nonstop1h 35m

Chicago O'Hare Intl

lun. 1/27

9:15 pm-10:37 pm

Nonstop1h 22m

$180

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

sáb. 1/18

12:50 pm-2:20 pm

Nonstop1h 30m

Chicago Midway

dom. 1/19

11:10 am-12:35 pm

Nonstop1h 25m

$197

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

vie. 1/10

6:00 pm-9:58 pm

1 stop3h 58m

Chicago O'Hare Intl

lun. 1/13

6:15 am-10:06 am

1 stop3h 51m

$198

WausauChicago

CWA - ORD

CWAORD

Wausau Central Wisconsin

sáb. 1/18

3:09 pm-4:28 pm

Nonstop1h 19m

Chicago O'Hare Intl

sáb. 1/25

12:25 pm-1:35 pm

Nonstop1h 10m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

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.

Travel insights for flights from Wisconsin to Chicago

Get recent, data-driven insights about flights from Wisconsin to Chicago including ideal travel times, pricing trends, and more.

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 $245). Flying from Wisconsin to Chicago in March is currently the most expensive (average of $317). 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 diciembre 19, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Chicago as you normally would.

Weekly flight availability from Wisconsin to Chicago

Explore weekly flight availability from Wisconsin 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 diciembre 19, 2024.

The most flights from USWI to CHI are scheduled on a Thursday (42 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (13 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 diciembre 19, 2024.
Read reviews from past customers who have flown United Airlines, Sun Country Air and American Airlines from Wisconsin to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,836 reviews

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,836 reviews
Southwest
8.1
Very good
4,836 reviews

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,551 reviews
Southwest
8.1
Very good
4,836 reviews

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,600 reviews
Southwest
8.1
Very good
4,836 reviews

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,048 reviews
Southwest
8.1
Very good
4,836 reviews

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,836 reviews

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • 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 $59 on Sun Country Air. Other airlines that offer cheap prices include Frontier from $60 and Delta from $69 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 Green Bay Austin-Straubel - 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 (94%), Qatar Airways (92%), Japan Airlines (91%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $1,236, our data indicates the cheapest price to be $146. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $116.

  • 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 $245). Flying from Wisconsin to Chicago in March is currently the most expensive (average of $317). 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 Wisconsin 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 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 diciembre 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$176Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$178Average$282FlexibilityNo cancel feeOn-time69%
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