Cheap flights from Wisconsin (WI) to Chicago (CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

How to find the cheapest flight from
Wisconsin to Chicago (CHI)

All the information you need to plan the best null to CHI flight in 2022: compare Wisconsin to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
What is the cheapest month to fly from Wisconsin to Chicago?

Our data shows that April tends to be the cheapest month to fly to Chicago from Wisconsin. Users have commonly found prices around $279 for the month, but tickets can be as low as $175. Due to multiple factors, prepare for potentially higher prices in June.

When is the cheapest time to fly from Wisconsin to Chicago (WI - CHI)?

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.

Cheap flights from Wisconsin to Chicago in January, February 2022

The best prices found for Wisconsin to CHI flights for January, February
17 Feb - 21 Feb
$78pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
16 Feb - 21 Feb
$79pp
GRB
Green Bay Austin-Straubel
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
GRB
Green Bay Austin-Straubel
13 Feb - 15 Feb
$88pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field

Wisconsin to Chicago 2022 flight deals

Cheap flights to Chicago from Wisconsin found for this year
17 Feb - 21 Feb
$78pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
1 Mar - 22 Mar
$78pp
MKE
Milwaukee Milwaukee-Mitchell
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MKE
Milwaukee Milwaukee-Mitchell
16 Feb - 21 Feb
$79pp
GRB
Green Bay Austin-Straubel
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
GRB
Green Bay Austin-Straubel

Non-stop flights to Chicago from Wisconsin

Save time with Wisconsin to Chicago direct flight deals
1 Mar - 22 Mar
$78pp
MKE
Milwaukee Milwaukee-Mitchell
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MKE
Milwaukee Milwaukee-Mitchell
17 Feb - 21 Feb
$78pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
16 Feb - 21 Feb
$79pp
GRB
Green Bay Austin-Straubel
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
GRB
Green Bay Austin-Straubel

Last minute flights from Wisconsin to Chicago

Late deals on round-trip flights to Chicago from Wisconsin, departing today and this week
4 Feb - 9 Feb
$216pp
GRB
Green Bay Austin-Straubel
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
GRB
Green Bay Austin-Straubel
4 Feb - 7 Feb
$219pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
   
2 STOPS
MSN
Madison Truax Field
3 Feb - 7 Feb
$220pp
EAU
Eau Claire
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EAU
Eau Claire

One-way flights to Chicago from Wisconsin

The cheapest one-way flights from Wisconsin to Chicago
12:30 am - 1:25 am
United Airlines
Nonstop
0h 55m
MKE - ORD
United Airlines
$49
United
9:55 am - 11:11 am
American Airlines
Nonstop
1h 16m
CWA - ORD
American Airlines
1:00 am - 6:50 pm
Spirit Airlines
1 Stop
17h 50m
MKE - ORD
Spirit Airlines
$106
Gotogate

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Wisconsin</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Wisconsin to Chicago

Which airlines flying from Wisconsin to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Wisconsin to Chicago that may be offering flexible cancellation policies are United Airlines, American Airlines, and Bus. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Wisconsin to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Wisconsin to Chicago for under $100. The cheapest flight booked recently is on United Airlines for just $78, but on average you can expect to pay $116.

Are there nonstop flights from Wisconsin to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Wisconsin to Chicago under $100. A good price for a nonstop flight from Wisconsin to Chicago is less than $127.

Are there last-minute flights available from Wisconsin to Chicago for under $300?

There are currently 20+ open flights from Wisconsin to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Wisconsin to Chicago?

Nonstop flights can be found on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

How many flights depart from Wisconsin to Chicago on average per day?

On average 23 flights depart from Wisconsin to Chicago per day.
Early Morning (Midnight to 6am) - 35% of flight departures
Morning (6am - Noon) - 48% of flight departures
Afternoon (Noon - 6pm) - 9% of flight departures
Evening (6pm - Midnight) - 9% of flight departures

How long is the flight from Wisconsin to Chicago?

A quick flight from Wisconsin to Chicago can take about 1h 02m. United Airlines provides one of the quickest options available for as low as $78. Wisconsin and Chicago are separated by a distance of 67 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 $39 on United Airlines. Other airlines that offer cheap prices include American Airlines from $40 and Spirit Airlines from $52 one-way.

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: Iberia (95%), Qatar Airways (95%), British Airways (90%).

What are the most popular routes from Wisconsin to Chicago?

The most popular route from Wisconsin to Chicago is Green Bay Austin-Straubel - Chicago O'Hare Intl. You may also consider Milwaukee Milwaukee-Mitchell - Chicago O'Hare Intl or Green Bay Austin-Straubel - Chicago Midway.

What are the cheapest flights from Wisconsin to Chicago?

Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $384, our data indicates the cheapest price to be $18. The most popular route (Green Bay Austin-Straubel - Chicago O'Hare Intl), is priced around $79.

What are the most popular airlines that fly from Wisconsin to Chicago?

The most popular airlines flying from Wisconsin to Chicago are Train, Bus and American Airlines. Something to consider prior to booking your flight.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Wisconsin?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Wisconsin need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Wisconsin must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Wisconsin are not required to quarantine after entering Chicago.

Do I need a test to fly back to Wisconsin from Chicago?

Returning to Wisconsin from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Wisconsin.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Wisconsin.

Hide COVID Travel Restrictions for Chicago, IL

Departure points for flights from Wisconsin to Chicago

Select to see more specific information for flights to Chicago from all departure points in Wisconsin.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Wisconsin to Chicago.
Flight duration from Wisconsin to Chicago
1h 04m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing

Sparta/Fort McCoy (CMY)
Wausau (CWA)
Eau Claire (EAU)
Green Bay (GRB)
La Crosse (LSE)
Milwaukee (MKE)

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)
Home North America USA Illinois Chicago Cheap flights from Wisconsin to Chicago