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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 8/28. 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
Mon 7/1
Mon 7/8

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Good to know

Low season

January

High season

July

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 33% 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 54m.

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

    46 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 325 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 Thursdays 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 Sundays.

  • 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. American Airlines offered a round-trip connection from $219 and United Airlines from $310.

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 10754 reviews
7.7Boarding
8.1Crew
7.2Comfort
6.7Food
7.1Entertainment
Airline reviews

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

8.0 ExcellentBob, Jun 2024ORD - LAX
Read more about United Airlines reviews

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

Book cheap flights from Chicago to Wisconsin Dells

Recent round-trip flight deals

8/28Wed
nonstopAmerican Airlines
1h 05mORD-MSN
8/31Sat
nonstopAmerican Airlines
1h 10mMSN-ORD
$219
6/26Wed
nonstopAmerican Airlines
0h 58mORD-MSN
7/3Wed
nonstopAmerican Airlines
1h 00mMSN-ORD
$229
7/1Mon
nonstopAmerican Airlines
1h 08mORD-MSN
7/8Mon
nonstopAmerican Airlines
0h 57mMSN-ORD
$249
6/22Sat
nonstopAmerican Airlines
1h 01mORD-MSN
6/26Wed
nonstopAmerican Airlines
1h 00mMSN-ORD
$259
6/22Sat
nonstopAmerican Airlines
1h 01mORD-MSN
6/29Sat
nonstopAmerican Airlines
1h 00mMSN-ORD
$279
6/27Thu
nonstopUnited Airlines
1h 02mORD-MSN
7/1Mon
nonstopUnited Airlines
1h 06mMSN-ORD
$310
6/30Sun
nonstopUnited Airlines
1h 02mORD-MSN
7/7Sun
nonstopUnited Airlines
1h 03mMSN-ORD
$339
6/27Thu
1 stopDelta
19h 53mORD-MSN
7/1Mon
2 stopsDelta
18h 05mMSN-ORD
$745
8/28Wed
3 stops
29h 19mORD-MSN
8/31Sat
2 stops
25h 45mMSN-ORD
$3,447
8/28Wed
3 stops
29h 19mORD-MSN
8/31Sat
3 stops
25h 45mMSN-ORD
$3,529

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Recent one-way flight deals

8/28Wed
nonstopAmerican Airlines
1h 11mORD-MSN
$110
7/17Wed
nonstopAmerican Airlines
1h 01mORD-MSN
$120
8/26Mon
nonstopAmerican Airlines
0h 58mORD-MSN
$130
6/21Fri
nonstopAmerican Airlines
1h 08mORD-MSN
$140
7/17Wed
1 stopAmerican Airlines
5h 50mORD-MSN
$159
11/27Wed
1 stopSun Country Air
6h 35mORD-MSN
$161
9/28Sat
1 stopAmerican Airlines
5h 34mORD-MSN
$168
6/18Tue
nonstopUnited Airlines
1h 05mORD-MSN
$222
6/21Fri
3 stops
25h 25mORD-MSN
$232
6/18Tue
2 stopsDelta
14h 26mORD-MSN
$431

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Last minute flights from Chicago to Wisconsin Dells

Last minute flight, train and bus deals

6/6Thu
nonstopAmerican Airlines
1h 08mORD-MSN
6/6Thu
nonstopAmerican Airlines
1h 00mMSN-ORD
$574
6/2Sun
nonstopUnited Airlines
1h 02mORD-MSN
6/3Mon
nonstopUnited Airlines
1h 08mMSN-ORD
$581
6/6Thu
nonstopAmerican Airlines
1h 08mORD-MSN
6/6Thu
multi-stopAmerican Airlines
6h 05mMSN-ORD
$583
6/2Sun
multi-stopAmerican Airlines
7h 51mORD-MSN
6/3Mon
nonstopAmerican Airlines
0h 59mMSN-ORD
$590
6/6Thu
multi-stopAmerican Airlines
5h 35mORD-MSN
6/6Thu
multi-stopAmerican Airlines
6h 05mMSN-ORD
$593
6/2Sun
multi-stopAmerican Airlines
5h 45mORD-MSN
6/3Mon
multi-stopAmerican Airlines
5h 48mMSN-ORD
$600
6/2Sun
multi-stopDelta
16h 52mORD-MSN
6/3Mon
multi-stopDelta
14h 55mMSN-ORD
$1,439

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Flights to Wisconsin Dells