Southwest Wisconsin Vacations from ₩1,240,666

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    Save up to ₩234,741 when you book a flight and hotel together*

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The Latest Southwest Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ₩1,611,162, price is now ₩1,240,666 per person
₩1,240,666
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
Clean room great hotel

Reviewed on Dec 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₩1,925,886, price is now ₩1,291,332 per person
₩1,291,332
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Jasmine was courteous and friendly, made our check in process smooth. Clean rooms and the breakfast was amazing. I definitely recommend staying here.

Reviewed on Dec 31, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩2,479,682, price is now ₩1,699,954 per person
₩1,699,954
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great time and staff

Reviewed on Dec 30, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ₩1,888,250, price is now ₩1,387,130 per person
₩1,387,130
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ₩1,900,232, price is now ₩1,447,446 per person
₩1,447,446
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Loved our stay, clean rooms and restroom. Located right in the heart of downtown and everything was within walking distance. The only complaint would be the poor lighting in the rooms, very dark and minimal lights. It was hard to find my belongings at times. Aside from that, we’d definitely stay again!

Reviewed on Dec 31, 2025

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
Madison showing a garden, a house and flowers

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

Find the Best Southwest Wisconsin Vacation Packages

Southwest Wisconsin Hotel Deals

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
9.4/10 Exceptional! (3,395 reviews)
Great hotel for a game at Camp Randall!! Go Hawks!!!!

Reviewed on Dec 26, 2025

Get rates
The Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is ₩151,232 per night from Jan 4 to Jan 5
₩151,232
₩174,673 total
Jan 4 - Jan 5, 2026
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
Very elegant, very homey, and impeccably clean. Plus, sleep, food, drinks, and shopping were all just minutes away - super convenient.

Reviewed on Dec 28, 2025

DoubleTree by Hilton Madison East
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is ₩98,476 per night from Jan 9 to Jan 10
₩98,476
₩113,741 total
Jan 9 - Jan 10, 2026
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Friendly, helpful and efficient staff. Large, quiet and clean room. Breakfast bar had a lot of choices and large seating area with a lot of tables and a community sized high top to share

Reviewed on Dec 29, 2025

Hampton Inn & Suites Madison-West
See all 3,675 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.

Discover the most popular places to visit in Southwest Wisconsin

Christmas Mountain

Hit the slopes at Christmas Mountain during your trip to Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.

Christmas Mountain

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 canceling 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 travelers 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. Travelers 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 vacationers 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 favorite 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.