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$83 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 6/5. 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
Fri 6/7
Fri 6/14

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In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

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Good to know

Low season

February

High season

August

Cheapest flight

$83
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

9/18Wed
nonstopAmerican Airlines
1h 10mGRB-ORD
10/1Tue
nonstopAmerican Airlines
1h 00mORD-GRB
$219
6/5Wed
nonstopUnited Airlines
1h 03mMSN-ORD
6/5Wed
nonstopUnited Airlines
1h 02mORD-MSN
$229
6/12Wed
nonstopAmerican Airlines
1h 12mATW-ORD
8/17Sat
nonstopAmerican Airlines
1h 02mORD-ATW
$234
5/29Wed
1 stopDelta
6h 23mATW-ORD
6/1Sat
1 stopDelta
5h 03mORD-ATW
$248
5/29Wed
2 stopsDelta
8h 49mATW-ORD
6/1Sat
1 stopDelta
3h 21mORD-ATW
$253
6/6Thu
2 stopsSpirit Airlines
15h 47mMKE-ORD
6/13Thu
2 stopsSpirit Airlines
17h 03mORD-MKE
$268
5/18Sat
1 stopSpirit Airlines
8h 25mMKE-ORD
5/21Tue
1 stopSpirit Airlines
6h 15mORD-MKE
$270
5/19Sun
2 stops
24h 55mMKE-ORD
5/21Tue
2 stops
18h 51mORD-MKE
$281
6/6Thu
2 stops
15h 47mMKE-ORD
6/13Thu
3 stops
28h 36mORD-MKE
$306
5/30Thu
1 stopAlaska Airlines
15h 07mMKE-ORD
6/2Sun
1 stopAlaska Airlines
16h 13mORD-MKE
$495

Search by stops

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Recent one-way flight deals

6/5Wed
1 stopSpirit Airlines
13h 15mMKE-ORD
$83
6/5Wed
2 stopsSpirit Airlines
14h 57mMKE-ORD
$88
8/14Wed
nonstopAmerican Airlines
1h 13mGRB-ORD
$110
9/3Tue
nonstopAmerican Airlines
1h 15mATW-ORD
$110
5/20Mon
3 stops
29h 50mATW-ORD
$113
5/26Sun
1 stopDelta
4h 37mATW-MDW
$124
5/26Sun
1 stopDelta
5h 42mATW-ORD
$124
6/24Mon
3 stops
26h 21mATW-ORD
$131
6/25Tue
nonstopUnited Airlines
1h 18mATW-ORD
$155
6/24Mon
nonstopUnited Airlines
1h 18mATW-ORD
$159

Search by stops

Search by airline

Search by price

Last minute flights from Wisconsin to Chicago

Last minute flight, train and bus deals

5/11Sat
multi-stopDelta
4h 48mGRB-MDW
5/14Tue
multi-stopDelta
3h 09mMDW-GRB
$563
5/11Sat
multi-stopDelta
4h 08mGRB-MDW
5/14Tue
multi-stopDelta
8h 03mMDW-GRB
$568
5/9Thu
nonstopUnited Airlines
1h 13mGRB-ORD
5/9Thu
nonstopUnited Airlines
1h 11mORD-GRB
$573
5/11Sat
multi-stopDelta
4h 48mGRB-MDW
5/14Tue
multi-stopDelta
3h 18mMDW-GRB
$573
5/11Sat
multi-stopDelta
4h 08mGRB-MDW
5/14Tue
multi-stopDelta
8h 03mMDW-GRB
$578
5/10Fri
nonstopAmerican Airlines
1h 11mATW-ORD
5/11Sat
nonstopAmerican Airlines
1h 11mORD-ATW
$579
5/10Fri
multi-stopAmerican Airlines
5h 20mATW-ORD
5/11Sat
nonstopAmerican Airlines
0h 58mORD-ATW
$587
5/10Fri
multi-stopAmerican Airlines
5h 20mATW-ORD
5/11Sat
multi-stopAmerican Airlines
6h 54mORD-ATW
$595
5/11Sat
multi-stopDelta
9h 55mGRB-MDW
5/14Tue
multi-stopDelta
8h 03mMDW-GRB
$663
5/13Mon
nonstopUnited Airlines
1h 03mMSN-ORD
5/14Tue
nonstopUnited Airlines
0h 55mORD-MSN
$673

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Wisconsin

Cabin classes:

$691
$993
$754
$245