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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
Sat 6/8
Sat 6/15

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In the last 7 days travelers have searched 43,895,468 times on KAYAK, and here is why:

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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

8/27Tue
nonstopAmerican Airlines
1h 03mMSN-ORD
9/24Tue
nonstopAmerican Airlines
1h 17mORD-MSN
$219
7/1Mon
nonstopAmerican Airlines
1h 02mMKE-ORD
7/5Fri
nonstopAmerican Airlines
1h 06mORD-MKE
$229
6/5Wed
2 stops
14h 23mATW-ORD
6/6Thu
2 stops
20h 06mORD-ATW
$234
5/29Wed
1 stopDelta
6h 23mATW-ORD
6/1Sat
1 stopDelta
5h 03mORD-ATW
$248
6/5Wed
3 stops
25h 31mATW-ORD
6/6Thu
2 stops
20h 06mORD-ATW
$250
5/29Wed
2 stopsDelta
8h 49mATW-ORD
6/1Sat
1 stopDelta
3h 21mORD-ATW
$253
5/30Thu
nonstopUnited Airlines
1h 03mMSN-ORD
6/2Sun
nonstopUnited Airlines
1h 05mORD-MSN
$254
6/1Sat
1 stopSpirit Airlines
14h 18mMKE-ORD
6/8Sat
1 stopSpirit Airlines
10h 35mORD-MKE
$276
6/6Thu
2 stopsSpirit Airlines
15h 47mMKE-ORD
6/13Thu
2 stopsSpirit Airlines
17h 03mORD-MKE
$279
5/29Wed
nonstopUnited Airlines
1h 18mATW-ORD
6/1Sat
nonstopUnited Airlines
1h 12mORD-ATW
$289

Search by stops

Search by airline

Search by price

Recent one-way flight deals

7/5Fri
1 stopSun Country Air
17h 13mMKE-ORD
$88
5/20Mon
2 stops
23h 15mATW-ORD
$98
6/5Wed
2 stops
9h 10mATW-ORD
$101
7/8Mon
1 stopSun Country Air
24h 04mMKE-ORD
$103
8/14Wed
nonstopAmerican Airlines
1h 13mGRB-ORD
$110
8/14Wed
nonstopAmerican Airlines
1h 03mMKE-ORD
$110
5/26Sun
1 stopDelta
4h 01mATW-ORD
$124
6/1Sat
2 stopsDelta
6h 17mATW-ORD
$129
6/7Fri
nonstopUnited Airlines
1h 03mMSN-ORD
$140
7/5Fri
nonstopUnited Airlines
1h 04mMKE-ORD
$145

Search by stops

Search by airline

Search by price

Last minute flights from Wisconsin to Chicago

Last minute flight, train and bus deals

5/14Tue
multi-stop
13h 56mMKE-ORD
5/18Sat
multi-stop
20h 32mORD-MKE
$439
5/12Sun
nonstopAmerican Airlines
1h 12mATW-ORD
8/19Mon
nonstopAmerican Airlines
1h 02mORD-ATW
$459
5/12Sun
multi-stopDelta
5h 00mATW-ORD
8/19Mon
multi-stopDelta
5h 08mORD-ATW
$478
5/14Tue
multi-stopSpirit Airlines
13h 56mMKE-ORD
5/21Tue
multi-stopSpirit Airlines
12h 53mORD-MKE
$479
5/14Tue
multi-stopSpirit Airlines
13h 56mMKE-ORD
5/21Tue
multi-stopSpirit Airlines
16h 49mORD-MKE
$487
5/14Tue
multi-stopSpirit Airlines
13h 56mMKE-ORD
5/21Tue
multi-stopSpirit Airlines
14h 16mORD-MKE
$493
5/14Tue
multi-stop
13h 56mMKE-ORD
5/18Sat
multi-stop
25h 52mORD-MKE
$495
5/14Tue
nonstopUnited Airlines
1h 03mMSN-ORD
5/15Wed
nonstopUnited Airlines
1h 02mORD-MSN
$509
5/12Sun
multi-stopDelta
5h 40mATW-MDW
8/19Mon
multi-stopDelta
3h 46mMDW-ATW
$548
5/13Mon
nonstopUnited Airlines
1h 04mMSN-ORD
5/20Mon
nonstopUnited Airlines
1h 00mORD-MSN
$877

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Wisconsin

Cabin classes:

$691
$993
$754
$245