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$102 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 5/29. 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 6/1
Sat 6/8

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In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

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Good to know

Low season

February

High season

March

Cheapest flight

$102
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 23% lower on average.
Flight from Madison 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, +78 more

ANA, Aer Lingus, +79 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, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 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, +78 more

ANA, Aer Lingus, +79 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, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Book cheap flights from Wisconsin to Chicago

Recent round-trip flight deals

5/28Tue
1 stopSpirit Airlines
17h 55mMKE-ORD
6/4Tue
2 stopsSpirit Airlines
18h 51mORD-MKE
$181
5/28Tue
1 stopSpirit Airlines
17h 55mMKE-ORD
6/4Tue
1 stopSpirit Airlines
15h 55mORD-MKE
$191
5/28Tue
1 stopSpirit Airlines
17h 55mMKE-ORD
6/4Tue
3 stopsSpirit Airlines
26h 32mORD-MKE
$195
5/29Wed
nonstopUnited Airlines
1h 15mGRB-ORD
6/5Wed
nonstopUnited Airlines
1h 12mORD-GRB
$229
5/29Wed
nonstopUnited Airlines
1h 04mMKE-ORD
6/5Wed
nonstopUnited Airlines
1h 00mORD-MKE
$229
8/27Tue
nonstopAmerican Airlines
1h 00mMSN-ORD
9/24Tue
nonstopAmerican Airlines
0h 57mORD-MSN
$229
5/28Tue
nonstopAmerican Airlines
1h 08mGRB-ORD
6/12Wed
nonstopAmerican Airlines
0h 59mORD-GRB
$239
5/29Wed
1 stopDelta
6h 17mGRB-MDW
6/5Wed
1 stopDelta
5h 55mMDW-GRB
$248
5/22Wed
1 stopDelta
4h 43mATW-ORD
5/25Sat
1 stopDelta
4h 25mORD-ATW
$248
5/25Sat
1 stop
14h 18mMKE-ORD
5/26Sun
2 stops
15h 21mORD-MKE
$273

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/29Wed
2 stops
21h 38mMSN-ORD
$102
6/23Sun
1 stopSun Country Air
24h 25mMKE-ORD
$113
5/31Fri
2 stopsSpirit Airlines
27h 03mMKE-ORD
$114
8/14Wed
nonstopAmerican Airlines
1h 12mGRB-ORD
$115
5/29Wed
nonstopAmerican Airlines
1h 06mATW-ORD
$115
5/22Wed
nonstopAmerican Airlines
0h 59mMSN-ORD
$115
5/29Wed
1 stopDelta
3h 38mATW-ORD
$124
5/18Sat
2 stops
10h 55mMSN-ORD
$128
5/31Fri
3 stopsSpirit Airlines
22h 20mMKE-ORD
$136
5/29Wed
1 stopDelta
3h 36mGRB-ORD
$154

Search by stops

Search by airline

Search by price

Last minute flights from Wisconsin to Chicago

Last minute flight, train and bus deals

5/5Sun
multi-stopSun Country Air
24h 18mMKE-ORD
5/12Sun
multi-stopSun Country Air
9h 57mORD-MKE
$307
5/5Sun
multi-stop
38h 53mMKE-ORD
5/12Sun
multi-stop
9h 57mORD-MKE
$359
5/5Sun
multi-stop
38h 53mMKE-ORD
5/12Sun
multi-stop
24h 56mORD-MKE
$455
5/6Mon
nonstopUnited Airlines
1h 03mMSN-ORD
5/23Thu
nonstopUnited Airlines
1h 05mORD-MSN
$459
5/4Sat
multi-stopSpirit Airlines
13h 03mMKE-ORD
5/7Tue
multi-stopSpirit Airlines
6h 39mORD-MKE
$466
5/5Sun
multi-stopAmerican Airlines
5h 17mMSN-ORD
5/24Fri
nonstopAmerican Airlines
0h 58mORD-MSN
$521
5/4Sat
multi-stopDelta
5h 17mGRB-ORD
5/15Wed
multi-stopDelta
6h 06mORD-GRB
$523
5/4Sat
nonstopUnited Airlines
1h 13mGRB-ORD
5/15Wed
nonstopUnited Airlines
1h 11mORD-GRB
$524
5/5Sun
multi-stopAmerican Airlines
5h 17mMSN-ORD
5/24Fri
multi-stopAmerican Airlines
7h 03mORD-MSN
$529
5/4Sat
multi-stopSpirit Airlines
15h 20mMKE-ORD
5/5Sun
multi-stopSpirit Airlines
26h 49mORD-MKE
$612

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Wisconsin

Cabin classes:

$682
$922
$742
$245