$122 Find Cheap Flights from Chicago to Wisconsin Dells - Compare and Save

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 8/25. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$238
American Airlines
Sun 8/9Sun 8/16
ORD - MSN • Non-stop
Cheapest one-way
$122
Typical prices: $278-$648
Multiple Airlines
Tue 8/25
ORD - MSN • 2 stops
Arrival airport
You can't fly directly to Wisconsin Dells. It is served by Madison (MSN), located 40.6 miles from Wisconsin Dells.
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Flight Deals
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Flight Deals

Cheap Flights from Chicago to Wisconsin Dells (CHI-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Wisconsin Dells that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Wisconsin Dells

Sun, Aug 9 - Sun, Aug 16
American Airlines Logo
9:30 pm - 10:39 pm
ORD
-
MSN
1h 09mnonstop
American Airlines Logo
9:48 am - 11:01 am
MSN
-
ORD
1h 13mnonstop
$238American Airlines
Tue, Jul 21 - Tue, Jul 28
United Airlines Logo
4:01 pm - 5:10 pm
ORD
-
MSN
1h 09mnonstop
United Airlines Logo
5:00 am - 6:17 am
MSN
-
ORD
1h 17mnonstop
$239United Airlines
Wed, Jul 8 - Sat, Jul 11
United Airlines Logo
7:45 pm - 8:57 pm
ORD
-
MSN
1h 12mnonstop
United Airlines Logo
5:45 pm - 7:00 pm
MSN
-
ORD
1h 15mnonstop
$269United Airlines
Tue, Sep 15 - Tue, Sep 22
American Airlines Logo
11:17 am - 12:26 pm
ORD
-
MSN
1h 09mnonstop
American Airlines Logo
5:00 am - 6:25 am
MSN
-
ORD
1h 25mnonstop
$287American Airlines
Sun, Jul 19 - Sun, Jul 26
United Airlines Logo
8:40 am - 9:47 am
ORD
-
MSN
1h 07mnonstop
United Airlines Logo
6:41 am - 7:54 am
MSN
-
ORD
1h 13mnonstop
$291United Airlines
Wed, Jul 22 - Sat, Jul 25
United Airlines Logo
10:35 am - 11:49 am
ORD
-
MSN
1h 14mnonstop
United Airlines Logo
5:00 am - 6:16 am
MSN
-
ORD
1h 16mnonstop
$293United Airlines
Wed, Sep 2 - Sat, Sep 5
United Airlines Logo
7:45 pm - 8:53 pm
ORD
-
MSN
1h 08mnonstop
United Airlines Logo
6:15 pm - 7:32 pm
MSN
-
ORD
1h 17mnonstop
$309United Airlines
Wed, Jul 22 - Wed, Jul 29
Delta Logo
9:54 am - 2:04 pm
MDW
-
MSN
4h 10m
1 stop
Delta Logo
2:45 pm - 6:18 pm
MSN
-
MDW
3h 33m
1 stop
$1,185Delta
Sun, Aug 9 - Sun, Aug 16
Delta Logo
7:25 pm - 11:00 pm
MDW
-
MSN
3h 35m
1 stop
Delta Logo
12:13 pm - 6:01 pm
MSN
-
MDW
5h 48m
1 stop
$1,225Delta
Wed, Jul 8 - Sat, Jul 11
Delta Logo
9:54 am - 2:04 pm
MDW
-
MSN
4h 10m
1 stop
Delta Logo
12:03 pm - 5:52 pm
MSN
-
MDW
5h 49m
1 stop
$1,245Delta
Useful Info

Good to know

Low seasonJuly
Cheapest flight$122
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly with an average 5% increase in price.
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 1h 01m.

  • 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 Thursday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays 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.

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 May, June and July. The cheapest month to fly is July.

Reviews of the top airline 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 9893 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

10.0 ExcellentNerissa, Jun 2026
ORD - ANC
Read more United Airlines reviews

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Everything you need to know for your flight from Chicago to Wisconsin Dells

Complete your trip to Wisconsin Dells with a hotel stay or car rental