Southwest Wisconsin Holidays

Photo by Inbal Arieh

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Southwest Wisconsin Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was S$1,114, price is now S$897 per person
S$897
per person
5 Jun - 7 Jun
found 19 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
missing the microwave. But other then that it was a good place for my family to stay there.

Reviewed on 25 Apr, 2026

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,477, price is now S$899 per person
S$899
per person
5 Jun - 7 Jun
found 19 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (2,177 reviews)
The hotel’s location is fantastic, putting you within walking distance of some great eats. Don't miss the rooftop bar; it has a cool indoor-outdoor setup that stays busy with locals and guests alike. It’s a bit of a splurge for drinks, but the atmosphere makes up for it. The rooms are a highlight—very modern and beautiful with great city views. As for the service, the staff was friendly and capable, though they felt a bit "all business" rather than warm. Definitely a comfortable place to call home for a few days.

Reviewed on 24 Apr, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,398, price is now S$970 per person
S$970
per person
5 Jun - 7 Jun
found 19 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value

Reviewed on 25 Apr, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was S$1,202, price is now S$922 per person
S$922
per person
5 Jun - 7 Jun
found 19 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (3,051 reviews)
Remodeled and very clean. Very convenient to hospital the next morning.

Reviewed on 22 Apr, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was S$1,432, price is now S$1,124 per person
S$1,124
per person
5 Jun - 7 Jun
found 19 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on 22 Apr, 2026

Where to stay in Southwest Wisconsin

Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Wisconsin
Wisconsin State Capitol building, view from Monona Terrace rooftop.; Shutterstock ID 5305432

Downtown Madison

The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip.

Find hotels in Downtown Madison

Top hotels in Southwest Wisconsin

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is S$184 per night from 24 May to 25 May
S$184
24 May - 25 May
includes taxes & fees
9.4/10 Exceptional! (3,676 reviews)
Great location; offers parking. Rooms are clean and modern as is the rest of the hotel. Bed was super comfy. Pool was a nice temperature and the pool area was very clean. Food we tried —especially desserts was delicious! Staff is friendly and helpful. We enjoyed our stay and will be back!

Reviewed on 26 Apr, 2026

The Madison Concourse Hotel and Governor's Club
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
The price is S$72 per night from 29 Apr to 30 Apr
S$72
29 Apr - 30 Apr
includes taxes & fees
7/10 Good! (2,722 reviews)
The room was nice sized and clean but there was no table so we could play games as a family.

Reviewed on 24 Apr, 2026

Mt. Olympus Water & Theme Park Resort
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
The price is S$171 per night from 10 May to 11 May
S$171
10 May - 11 May
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Staff wasn’t always knowledgeable.

Reviewed on 22 Apr, 2026

Great Wolf Lodge Wisconsin Dells
See all 3,755 properties in Southwest Wisconsin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

East Towne Mall

East Towne Mall

You can enjoy retail therapy at East Towne Mall during your trip to Madison. Savour the lively bars and top-notch restaurants while in town.

East Towne Mall
Casino hotel and convention center by Upper Mississippi on calm misty morning at Dubuque Iowa

Q Casino

Why not roll the dice with a visit to Q Casino during your visit to Dubuque? Make time to visit the area's casinos or simply enjoy its top-notch restaurants.

Q Casino

Outlets at The Dells

You can enjoy retail therapy at Outlets at The Dells during your trip to Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

Outlets at The Dells

Frequently asked questions

Can I cancel my flight booking to Southwest Wisconsin due to COVID-19?
Our Customer Service Portal is where you can get important information about changing or cancelling your flight due to COVID-19. Before you reserve a seat, it's a good idea to look over the terms and conditions of your preferred carrier too.
What's the best way to find cheap flights to Southwest Wisconsin that have flexible change policies?
It's as easy as counting to three with Expedia. First, enter your preferred travel dates and press "Search." Step 2: Check the "No change fee" box below the "Flexible change policies" subheading on the left-hand side of your screen. Step 3. Reserve your flexible and cheap ticket to Southwest Wisconsin.
What are some of the general tips for travellers to Southwest Wisconsin during the COVID-19 outbreak?
With new rules, restrictions and safety measures to follow, travel looks a bit different these days. These are some helpful things to know before you hop on that plane to Southwest Wisconsin:
  • Investigate if any travel restrictions apply to your origin and destination before locking in a flight. Also check if there are any requirements you'll need to follow on arrival, such as taking a COVID-19 test.
  • When you pass through airport screening, do not remove your face mask. You will be asked to lower it briefly for identification purposes. Travellers who refuse to wear a mask may face civil penalties and may also be escorted from the terminal.
  • Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. Once that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now allowed in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag at the X-ray machine for scanning.
  • To minimize handling during the screening process, put items such as your belt, phone and wallet into your carry-on instead of into the bins.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on makes it less likely that a TSA agent will need to touch and open your bag for inspection.

Which airlines fly to Southwest Wisconsin?
Arrange your airfare with United Airlines and then start piecing together your Southwest Wisconsin to-do list. This leading airline provides 238 flights every month to Dane County Regional Airport (MSN), a major gateway.
How can I find cheap tickets to Southwest Wisconsin?
In the last seven days, was the best price for a flight to Southwest Wisconsin. If you want to save even more, book ahead of time and be flexible with your travel dates. Search for your flight to Southwest Wisconsin, then see prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Southwest Wisconsin?
The cost of a round-trip flight to Southwest Wisconsin in the last seven days fluctuated between and . If you were heading one way from (), you could have landed a cheap fare from only .
What are the most popular airports to fly into in Southwest Wisconsin?
Jet into Dane County Regional Airport (MSN) and enjoy all that Southwest Wisconsin has to offer. As the region's main entry point, around 1068 flights touch down here each month.
When is the cheapest time to fly to Southwest Wisconsin?
If you can be flexible with what date you travel to Southwest Wisconsin, try to fly out earlier in the week. The most economical day to take off is usually Tuesday, followed by Monday. Saturday is typically the costliest day, with many holiday makers opting to take off on the weekend.
How much is a plane ticket to Southwest Wisconsin?
In the last seven days, fares varied between and . Have a look at our fantastic deals to Southwest Wisconsin, pick your favourite and then start packing your bags.
Which airlines with flights to Southwest Wisconsin employ COVID-19 cleanliness policies?
In response to the current pandemic, many airlines have adopted extra rules and standards to help their passengers fly with peace of mind. Check out what these carriers are doing:
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.