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Find cheap flights from Chicago to Wisconsin Dells from $110

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Wisconsin Dells departing on 9/21. 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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Good to know

Low season

January

High season

August

Cheapest flight

$110
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago O'Hare Airport to Madison

When to book flights from Chicago to Wisconsin Dells

Are your dates flexible? Find out the best times to travel from Chicago to Wisconsin Dells based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Wisconsin Dells

  • Which airports will I be using when flying from Chicago to Wisconsin Dells?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Wisconsin Dells does not have its own airport so you’ll be flying into nearby Madison Truax Field airport, which is 40.6 mi away.

  • How long does a flight from Chicago to Wisconsin Dells take?

    Direct flights cover the 123 miles separating Chicago and Wisconsin Dells in about 0h 58m.

  • How many flights are there between Chicago and Wisconsin Dells?

    47 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 335 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Wisconsin Dells?

    Consider leaving on a Wednesday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Fridays.

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

    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 Chicago to Wisconsin Dells.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Wisconsin Dells?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Wisconsin Dells from Chicago 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 Chicago to Wisconsin Dells?

    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 Wisconsin Dells with an airline and back to Chicago with another airline.

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

    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 Wisconsin Dells from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Wisconsin Dells?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Wisconsin Dells found on KAYAK was with American Airlines for $110. United Airlines offered a round-trip connection from $229 and American Airlines from $253.

See more FAQs

Top tips for finding cheap flights from Chicago to Wisconsin Dells

  • There is no airport in Wisconsin Dells. Instead, you’ll be flying into Madison Truax Field Airport when flying between Chicago and Wisconsin Dells.
  • High season is considered to be November, December and January. The cheapest month to fly is July.

Top airlines flying from Chicago to Wisconsin Dells

 
Need help choosing which airline to fly with from Chicago to Wisconsin Dells? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 11027 reviews
7.1Entertainment
7.2Comfort
7.7Boarding
8.1Crew
6.7Food
Airline reviews

I’ve had a couple flights this week on United that were delayed by an hour or more

4.0 OkayJared R., May 2024ORD - SFO
Read more about United Airlines reviews

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to Wisconsin Dells

Recent round-trip flight deals

5/29Wed
nonstopUnited Airlines
1h 08mORD-MSN
5/31Fri
nonstopUnited Airlines
1h 03mMSN-ORD
$229
7/5Fri
nonstopAmerican Airlines
1h 01mORD-MSN
7/8Mon
nonstopAmerican Airlines
0h 57mMSN-ORD
$253
6/14Fri
nonstopAmerican Airlines
0h 58mORD-MSN
6/18Tue
nonstopAmerican Airlines
1h 00mMSN-ORD
$264
8/27Tue
nonstopUnited Airlines
1h 03mORD-MSN
8/31Sat
nonstopUnited Airlines
1h 01mMSN-ORD
$279
6/7Fri
nonstopAmerican Airlines
0h 58mORD-MSN
6/14Fri
nonstopAmerican Airlines
1h 00mMSN-ORD
$298
7/7Sun
nonstopAmerican Airlines
0h 59mORD-MSN
7/18Thu
nonstopAmerican Airlines
1h 13mMSN-ORD
$317
6/6Thu
nonstopAmerican Airlines
0h 58mORD-MSN
6/9Sun
nonstopAmerican Airlines
1h 00mMSN-ORD
$328
8/27Tue
1 stopUnited Airlines
12h 16mORD-MSN
8/31Sat
nonstopUnited Airlines
1h 01mMSN-ORD
$357
8/27Tue
1 stopDelta
9h 15mMDW-MSN
8/31Sat
1 stopDelta
12h 06mMSN-MDW
$394
8/27Tue
1 stopDelta
12h 19mORD-MSN
8/31Sat
1 stopDelta
9h 35mMSN-ORD
$424

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Recent one-way flight deals

9/21Sat
nonstopAmerican Airlines
0h 55mORD-MSN
$110
6/5Wed
nonstopAmerican Airlines
0h 58mORD-MSN
$115
7/17Wed
nonstopAmerican Airlines
1h 00mORD-MSN
$125
6/8Sat
nonstopAmerican Airlines
0h 54mORD-MSN
$140
5/26Sun
nonstopUnited Airlines
1h 05mORD-MSN
$145
6/20Thu
nonstopUnited Airlines
1h 02mORD-MSN
$170
6/21Fri
2 stops
20h 59mORD-MSN
$207
6/21Fri
1 stop
14h 56mORD-MSN
$223
5/26Sun
3 stopsWestJet
23h 02mORD-MSN
$1,570
6/5Wed
3 stopsLufthansa
29h 10mORD-MSN
$2,913

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Flights to Wisconsin Dells