Find cheap flights from Wisconsin to Chicago

Find cheap flights from Wisconsin to Chicago

Round-trip
Economy
Boston (BOS)
Chicago All airports
Sat 8/1
Sat 8/8
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

Good to know

Low season

November Best time to beat the crowds with an average 7% drop in price.

High season

July Most popular time to fly with an average 24% increase in price.

Average price of a round-trip

$254 (avg. price over the last 2 weeks)

Good deal for a round-trip

$25 or less

FAQs for booking Wisconsin to Chicago flights

How does KAYAK find such low prices on flights from Wisconsin to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Wisconsin to Chicago?

What is the Hacker Fare option on flights from Wisconsin to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Wisconsin to Chicago?

Top airline flying from Wisconsin to Chicago

Scores according to KAYAK customer reviews

8.0
Delta
Overall score based on 28,491 reviews
8.2
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews
Read more about Delta

Book cheap flights from Wisconsin to Chicago (round-trip)

Airports
Origin
Milwaukee
$97
only
$97
Green Bay
$164
only
$164
Madison
$197
only
$197
La Crosse
$182
only
$182
Wausau
$198
only
$198
Appleton
$180
only
$180
Destination
Chicago
$97
only
$97
$182
only
$182
Sat, Aug 1
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
0h 57m
Wed, Aug 5
ORD
Chicago O'Hare Airport
MKE
Milwaukee-Mitchell Airport
0h 44m
Trip: 5 days
Based on null reviews
Fri, Sep 11
LSE
La Crosse
MDW
Chicago Midway Airport
3h 11m
Sun, Sep 13
MDW
Chicago Midway Airport
LSE
La Crosse
2h 55m
Trip: 3 days
Based on null reviews
Sat, Aug 1
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
0h 52m
Wed, Aug 5
ORD
Chicago O'Hare Airport
MKE
Milwaukee-Mitchell Airport
5h 07m
Trip: 5 days
Based on null reviews
Thu, Jul 30
GRB
Green Bay Austin-Straubel
ORD
Chicago O'Hare Airport
21h 57m
Sun, Aug 2
ORD
Chicago O'Hare Airport
GRB
Green Bay Austin-Straubel
9h 22m
Trip: 4 days
Based on null reviews
Sat, Sep 26
LSE
La Crosse
ORD
Chicago O'Hare Airport
5h 41m
Mon, Sep 28
ORD
Chicago O'Hare Airport
LSE
La Crosse
6h 20m
Trip: 3 days
Based on null reviews
Fri, Nov 13
CWA
Wausau Central Wisconsin
ORD
Chicago O'Hare Airport
8h 23m
Mon, Nov 23
ORD
Chicago O'Hare Airport
CWA
Wausau Central Wisconsin
6h 04m
Trip: 11 days
Based on null reviews
Sat, Aug 1
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
17h 31m
Wed, Aug 5
ORD
Chicago O'Hare Airport
ATW
Appleton Outagamie County
14h 05m
Trip: 5 days
Based on null reviews
Sat, Aug 1
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
17h 31m
Tue, Aug 4
ORD
Chicago O'Hare Airport
ATW
Appleton Outagamie County
21h 06m
Trip: 4 days
Based on null reviews
Wed, Aug 5
GRB
Green Bay Austin-Straubel
ORD
Chicago O'Hare Airport
5h 59m
Thu, Aug 6
ORD
Chicago O'Hare Airport
GRB
Green Bay Austin-Straubel
4h 41m
Trip: 2 days
Based on null reviews
Sun, Sep 20
GRB
Green Bay Austin-Straubel
ORD
Chicago O'Hare Airport
3h 36m
Tue, Sep 22
ORD
Chicago O'Hare Airport
GRB
Green Bay Austin-Straubel
4h 14m
Trip: 3 days
Based on null reviews
Sat, Aug 1
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
0h 59m
Wed, Aug 5
ORD
Chicago O'Hare Airport
ATW
Appleton Outagamie County
0h 57m
Trip: 5 days
Based on null reviews
Thu, Aug 27
MSN
Madison Truax Field
ORD
Chicago O'Hare Airport
1h 01m
Mon, Aug 31
ORD
Chicago O'Hare Airport
MSN
Madison Truax Field
0h 52m
Trip: 5 days
Based on null reviews
Thu, Jul 30
GRB
Green Bay Austin-Straubel
ORD
Chicago O'Hare Airport
6h 24m
Sun, Aug 2
ORD
Chicago O'Hare Airport
GRB
Green Bay Austin-Straubel
4h 41m
Trip: 4 days
Based on null reviews
Wed, Aug 5
GRB
Green Bay Austin-Straubel
ORD
Chicago O'Hare Airport
1h 05m
Thu, Aug 6
ORD
Chicago O'Hare Airport
GRB
Green Bay Austin-Straubel
1h 09m
Trip: 2 days
Based on null reviews
Wed, Aug 5
GRB
Green Bay Austin-Straubel
ORD
Chicago O'Hare Airport
5h 45m
Wed, Aug 5
ORD
Chicago O'Hare Airport
GRB
Green Bay Austin-Straubel
1h 01m
Trip: 1 days
Based on null reviews
Sat, Dec 5
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
15h 44m
Wed, Dec 9
ORD
Chicago O'Hare Airport
ATW
Appleton Outagamie County
10h 45m
Trip: 5 days
Based on null reviews
Sat, Aug 15
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
1h 06m
Sun, Aug 16
ORD
Chicago O'Hare Airport
ATW
Appleton Outagamie County
0h 56m
Trip: 2 days
Based on null reviews
Tue, Sep 22
MSN
Madison Truax Field
ORD
Chicago O'Hare Airport
6h 57m
Fri, Sep 25
ORD
Chicago O'Hare Airport
MSN
Madison Truax Field
15h 48m
Trip: 4 days
Based on null reviews
Tue, Nov 17
MSN
Madison Truax Field
ORD
Chicago O'Hare Airport
1h 01m
Sun, Nov 22
ORD
Chicago O'Hare Airport
MSN
Madison Truax Field
1h 05m
Trip: 6 days
Based on null reviews
Sat, Dec 5
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
15h 44m
Wed, Dec 9
ORD
Chicago O'Hare Airport
ATW
Appleton Outagamie County
8h 51m
Trip: 5 days
Based on null reviews

Book cheap flights from Wisconsin to Chicago (one-way)

Airports
Origin
Milwaukee
$83
only
$83
Green Bay
$103
only
$103
Eau Claire
$2208
only
$2208
Wausau
$148
only
$148
Appleton
$89
only
$89
Destination
Chicago
$83
only
$83
Mon, Aug 3
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
23h 53m
Based on null reviews
Tue, Aug 4
GRB
Green Bay Austin-Straubel
ORD
Chicago O'Hare Airport
5h 45m
Based on null reviews
Sat, Aug 1
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
10h 24m
Based on null reviews
Sat, Aug 15
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
28h 59m
Based on null reviews
Mon, Aug 17
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
24h 42m
Based on null reviews
Sun, Aug 23
CWA
Wausau Central Wisconsin
ORD
Chicago O'Hare Airport
6h 01m
Based on null reviews
Mon, Aug 3
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
0h 36m
$1135
Based on null reviews
Mon, Aug 3
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
9h 00m
$1139
Based on null reviews
Mon, Aug 17
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
9h 00m
$1202
Based on null reviews
Mon, Aug 17
MKE
Milwaukee-Mitchell Airport
ORD
Chicago O'Hare Airport
0h 36m
$1206
Based on null reviews
Sat, Aug 15
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
1h 17m
$1568
Based on null reviews
Sat, Aug 15
ATW
Appleton Outagamie County
ORD
Chicago O'Hare Airport
8h 19m
$1572
Based on null reviews
Sun, Aug 23
CWA
Wausau Central Wisconsin
ORD
Chicago O'Hare Airport
1h 40m
$1898
Based on null reviews
Sun, Aug 23
CWA
Wausau Central Wisconsin
ORD
Chicago O'Hare Airport
10h 18m
$1902
Based on null reviews
Mon, Aug 17
EAU
Eau Claire
ORD
Chicago O'Hare Airport
2h 05m
$2208
Based on null reviews
Mon, Aug 17
EAU
Eau Claire
ORD
Chicago O'Hare Airport
10h 45m
$2212
Based on null reviews
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
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