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$79 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 5/28. 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
Tue 5/28
Tue 6/4

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In the last 7 days travelers have searched 43,623,357 times on KAYAK, and here is why:

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Good to know

Low season

February

High season

March

Cheapest flight

$79
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 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, +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

7/5Fri
nonstopAmerican Airlines
1h 12mATW-ORD
7/13Sat
nonstopAmerican Airlines
1h 20mORD-ATW
$212
9/11Wed
nonstopAmerican Airlines
1h 10mGRB-ORD
9/17Tue
nonstopAmerican Airlines
1h 00mORD-GRB
$219
5/27Mon
2 stops
28h 25mMKE-ORD
6/3Mon
2 stops
19h 06mORD-MKE
$226
6/3Mon
1 stopSpirit Airlines
8h 25mMKE-ORD
6/4Tue
1 stopSpirit Airlines
6h 15mORD-MKE
$233
5/25Sat
1 stopDelta
4h 13mATW-MDW
6/1Sat
1 stopDelta
3h 53mMDW-ATW
$238
5/27Mon
2 stops
28h 25mMKE-ORD
6/3Mon
1 stop
7h 46mORD-MKE
$246
6/3Mon
1 stopSpirit Airlines
15h 57mMKE-ORD
6/4Tue
3 stopsSpirit Airlines
26h 32mORD-MKE
$261
6/22Sat
1 stopDelta
4h 48mATW-ORD
6/26Wed
1 stopDelta
5h 25mORD-ATW
$262
6/8Sat
nonstopUnited Airlines
1h 15mGRB-ORD
6/9Sun
nonstopUnited Airlines
1h 11mORD-GRB
$279
6/18Tue
nonstopUnited Airlines
1h 18mATW-ORD
6/25Tue
nonstopUnited Airlines
1h 11mORD-ATW
$299

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/28Tue
1 stopSpirit Airlines
17h 55mMKE-ORD
$79
5/27Mon
2 stops
28h 25mMKE-ORD
$102
5/18Sat
nonstopAmerican Airlines
1h 01mMKE-ORD
$110
5/18Sat
nonstopAmerican Airlines
0h 59mMSN-ORD
$110
5/28Tue
3 stopsSpirit Airlines
28h 40mMKE-ORD
$115
6/16Sun
1 stopDelta
5h 43mATW-MDW
$133
6/13Thu
1 stopDelta
5h 43mGRB-MDW
$149
7/12Fri
nonstopUnited Airlines
1h 16mGRB-ORD
$225
5/18Sat
1 stopUnited Airlines
17h 18mMKE-ORD
$227
10/2Wed
3 stopsWestJet
30h 49mMSN-ORD
$507

Search by stops

Search by airline

Search by price

Last minute flights from Wisconsin to Chicago

Last minute flight, train and bus deals

5/1Wed
multi-stop
24h 52mMSN-ORD
5/8Wed
multi-stop
6h 46mORD-MSN
$335
5/1Wed
multi-stop
37h 23mMSN-ORD
5/8Wed
multi-stop
6h 46mORD-MSN
$442
5/2Thu
multi-stop
11h 01mMKE-ORD
5/5Sun
multi-stop
7h 31mORD-MKE
$527
5/3Fri
nonstopAmerican Airlines
1h 13mATW-ORD
5/5Sun
nonstopAmerican Airlines
1h 05mORD-ATW
$544
5/2Thu
nonstopUnited Airlines
1h 05mMKE-ORD
5/5Sun
nonstopUnited Airlines
1h 02mORD-MKE
$544
5/1Wed
nonstopUnited Airlines
1h 07mMSN-ORD
5/5Sun
nonstopUnited Airlines
1h 02mORD-MSN
$544
5/3Fri
multi-stopAmerican Airlines
5h 15mATW-ORD
5/5Sun
nonstopAmerican Airlines
1h 05mORD-ATW
$552
4/30Tue
multi-stopSpirit Airlines
13h 30mMKE-ORD
5/1Wed
multi-stopSpirit Airlines
6h 25mORD-MKE
$561
5/3Fri
multi-stopDelta
6h 03mATW-ORD
5/5Sun
multi-stopDelta
5h 06mORD-ATW
$563
5/2Thu
multi-stopDelta
3h 30mCWA-MDW
5/5Sun
multi-stopDelta
3h 47mMDW-CWA
$600

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Wisconsin

Cabin classes:

$680
$556
$729
$241