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$88 Find cheap flights from Wisconsin to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 7/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
週日 6/9
週日 6/16

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Good to know

Low season

February

High season

August

Cheapest flight

$88
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 13% increase in price.
Flight from Milwaukee to Chicago O'Hare Airport

FAQs for booking flights from Wisconsin to Chicago

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Wisconsin is likely to change within 7 days, so travelers know whether to wait or book now.

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

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Wisconsin with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Wisconsin to Chicago?

Find which airlines fly direct from Wisconsin to Chicago, which days they fly and book direct flights.

Nonstop departures

Wisconsin to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Wisconsin

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Book cheap flights from Wisconsin to Chicago

Recent round-trip flight deals

8/13週二
nonstopAmerican Airlines
1h 13mGRB-ORD
8/20週二
nonstopAmerican Airlines
1h 08mORD-GRB
$219
8/27週二
nonstopAmerican Airlines
1h 03mMSN-ORD
9/24週二
nonstopAmerican Airlines
1h 17mORD-MSN
$219
7/1週一
1 stopDelta
5h 05mATW-MDW
7/5週五
1 stopDelta
3h 29mMDW-ATW
$248
5/29週三
1 stopDelta
3h 38mATW-ORD
6/1週六
1 stopDelta
5h 03mORD-ATW
$248
6/20週四
nonstopUnited Airlines
1h 13mGRB-ORD
7/3週三
nonstopUnited Airlines
1h 11mORD-GRB
$257
6/1週六
1 stopSpirit Airlines
13h 19mMKE-ORD
6/8週六
1 stopSpirit Airlines
8h 17mORD-MKE
$276
6/6週四
2 stopsSpirit Airlines
15h 47mMKE-ORD
6/13週四
2 stopsSpirit Airlines
17h 03mORD-MKE
$279
5/29週三
nonstopUnited Airlines
1h 18mATW-ORD
6/1週六
nonstopUnited Airlines
1h 09mORD-ATW
$289
5/23週四
2 stops
12h 10mMKE-ORD
5/30週四
2 stops
16h 51mORD-MKE
$356
5/23週四
2 stops
12h 10mMKE-ORD
5/30週四
1 stop
17h 39mORD-MKE
$363

Search by stops

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Recent one-way flight deals

7/5週五
1 stopSun Country Air
17h 13mMKE-ORD
$88
5/20週一
2 stops
24h 20mATW-ORD
$98
7/8週一
1 stopSun Country Air
24h 04mMKE-ORD
$103
5/31週五
nonstopAmerican Airlines
1h 11mATW-ORD
$115
7/1週一
nonstopAmerican Airlines
1h 01mMKE-ORD
$115
6/1週六
1 stopDelta
5h 42mGRB-ORD
$124
6/1週六
1 stopDelta
5h 00mATW-ORD
$124
7/9週二
nonstopAmerican Airlines
1h 03mMKE-ORD
$125
6/6週四
nonstopUnited Airlines
1h 15mGRB-ORD
$140
6/7週五
nonstopUnited Airlines
1h 03mMSN-ORD
$140

Search by stops

Search by airline

Search by price

Last minute flights from Wisconsin to Chicago

Last minute flight, train and bus deals

5/15週三
multi-stopSpirit Airlines
14h 06mMKE-ORD
5/18週六
multi-stopSpirit Airlines
13h 26mORD-MKE
$416
5/15週三
multi-stop
32h 34mATW-ORD
6/12週三
multi-stop
11h 10mORD-ATW
$431
5/15週三
multi-stopSpirit Airlines
14h 06mMKE-ORD
5/18週六
multi-stopSpirit Airlines
16h 21mORD-MKE
$439
5/15週三
nonstopAmerican Airlines
1h 11mATW-ORD
6/12週三
nonstopAmerican Airlines
1h 11mORD-ATW
$444
5/15週三
multi-stopSpirit Airlines
27h 40mMKE-ORD
5/18週六
multi-stopSpirit Airlines
16h 21mORD-MKE
$447
5/12週日
nonstopAmerican Airlines
1h 12mATW-ORD
8/19週一
nonstopAmerican Airlines
1h 02mORD-ATW
$459
5/12週日
multi-stopDelta
5h 00mATW-ORD
8/19週一
multi-stopDelta
5h 08mORD-ATW
$478
5/12週日
multi-stopDelta
5h 40mATW-MDW
8/19週一
multi-stopDelta
3h 46mMDW-ATW
$548
5/15週三
nonstopUnited Airlines
1h 19mATW-ORD
6/12週三
multi-stopUnited Airlines
16h 02mORD-ATW
$571
5/12週日
nonstopUnited Airlines
1h 19mATW-ORD
5/13週一
nonstopUnited Airlines
1h 04mORD-ATW
$579

Search by stops

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Search by price

Flights to Chicago

Return flight deals:

Chicago - Wisconsin

Cabin classes:

$691
$993
$754
$245