$137 Cheap flight deals from Chicago (CHI) to Baraboo (MSN)

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This Weekend's Flight Deals from Chicago to Baraboo

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 2 - Tue, Jan 20
ORD
O'Hare Intl.
MSN
Dane County Regional
$277 Roundtrip, found 6 days ago
$277
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Dane County Regional, returning Tue, Jan 20, priced at $277 found 6 days ago
Fri, Jan 2 - Sat, Jan 10
MDW
Midway Intl.
MSN
Dane County Regional
$1,098 Roundtrip, found 1 day ago
$1,098
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 2 from Midway Intl. to Dane County Regional, returning Sat, Jan 10, priced at $1,098 found 1 day ago

Airfares from $137 One Way, $179 Round Trip from Chicago to Baraboo

Prices starting at $179 for return flights and $137 for one-way flights to Baraboo were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Feb 20 - Sun, Feb 22
ORD
Chicago
MSN
Madison
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 20 from Chicago to Madison, returning Sun, Feb 22, priced at $179 found 1 day ago
Fri, Feb 20 - Sun, Feb 22
ORD
Chicago
MSN
Madison
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select United flight, departing Fri, Feb 20 from Chicago to Madison, returning Sun, Feb 22, priced at $179 found 1 day ago
Fri, Feb 20 - Sun, Feb 22
ORD
Chicago
MSN
Madison
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 20 from Chicago to Madison, returning Sun, Feb 22, priced at $209 found 1 day ago
Fri, Feb 20 - Sun, Feb 22
ORD
Chicago
MSN
Madison
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select United flight, departing Fri, Feb 20 from Chicago to Madison, returning Sun, Feb 22, priced at $218 found 1 day ago
Fri, Feb 20 - Sun, Feb 22
ORD
Chicago
MSN
Madison
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 20 from Chicago to Madison, returning Sun, Feb 22, priced at $219 found 1 day ago

Baraboo economy flight packages

Price found within the past 48 hours. Click for updated prices.
Polynesian Hotel & Suites Wisconsin Dells/Lake Delton
3.0-star property

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

5.8/10 (982 reviews)

Feb 15 - Feb 18

3 night stay

Chicago (CHI) to Madison (MSN)

American Airlines • Roundtrip • Coach
Price was $372, price is now $317 per person
$317
per person
found 1 day ago
The only thing was we couldn’t enjoy the water park area. The hot tub was full of little kids jumping into it. And no rules seemed to be followed. Might as well not have life guards on site. The second night was worse we spent about 5 minutes in there before we had to leave due to the smell of marijuana. The 3rd night we didn’t even bother to go back.

Reviewed on Oct 24, 2025

Christmas Mountain Campground
3.0-star property

Christmas Mountain Campground

9/10 Wonderful! (77 reviews)

Feb 15 - Feb 18

3 night stay

Chicago (CHI) to Madison (MSN)

American Airlines • Roundtrip • Coach
Price was $515, price is now $416 per person
$416
per person
found 1 day ago
I liked the properties location, the cabins looked so nice i enjoyed riding around on my electric scooter. What i didnt like was the inside of our cabin, it smelled old and not clean with a musty smell. It felt humid and the couches and table felt dirty. My son and husband went to the indoor pool and the next day my 7 year old has his first pink eye, we werent able to do anything the second day bc we didnt want him to contaminate anyone, Maybe from the pool? Cant say for sure but I'm sure that water was contaminated.

Reviewed on Jul 8, 2024

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort
3.0-star property

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

8.4/10 Very Good! (122 reviews)

Feb 15 - Feb 18

3 night stay

Chicago (CHI) to Madison (MSN)

American Airlines • Roundtrip • Coach
Price was $517, price is now $431 per person
$431
per person
found 1 day ago
We honestly really do love coming to this resort. This was our third stay, twice as Bluegreen owners, and this was the first time we have stayed since we gave up our ownership. But there is obviously a reason that we came back. We just love that it’s nestled in the woods, very quiet, the outdoor hot tub has always been a plus, especially in the mornings when it’s adult only swim. We have stayed in three of the different types of rooms and they have all been great. They’re spacious, clean, and have all the amenities you need to cook or have a relaxing night in by the fireplace. Mulligans is a great place for some food or a beer after a game of golf. There’s also a Starbucks for coffee in the morning and a small convenience store attached to it for other things that you might need. There’s also a lot of fun things for kids to do. We have done the mini golf and the paddle boating in the past, which is all included with your stay. And you also get discounts throughout town at certain restaurants and attractions. We will definitely be back!

Reviewed on Apr 14, 2024

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More About Flying To Baraboo from Chicago

Route Information for Flights from Chicago to Baraboo

Origin Airport IATA Code
CHI
Destination Airport IATA Code
MSN
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Baraboo

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.