Southwest Wisconsin, WI Vacation Packages

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Fairmont Chicago at Millennium Park Gold Experience
4.5-star property

Fairmont Chicago at Millennium Park Gold Experience

Downtown Chicago
9.2/10 Wonderful! (95 reviews)

Jun 3 - Jun 7

4 night stay

Boston (BOS) to Chicago (ORD)

United • Coach

Chicago (ORD) to Boston (BOS)

Spirit Airlines • Coach
Save 100% on your flight
per person
Chicago Marriott Downtown Magnificent Mile
4.0-star property

Chicago Marriott Downtown Magnificent Mile

Downtown Chicago
8.4/10 Very Good! (1,007 reviews)

Jun 15 - Jun 18

3 night stay

Boston (BOS) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
This property was very nice and there were eating options and a great bar/lounge.

Reviewed on Apr 22, 2024

Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

Downtown Chicago
8/10 Very Good! (1,178 reviews)

Jun 15 - Jun 18

3 night stay

Boston (BOS) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
This hotel has so much history. It’s so beautiful. Great food in the restaurant and you have to try the brownie! I would live here if I could.

Reviewed on Mar 25, 2024

DoubleTree by Hilton Chicago - Magnificent Mile
4.0-star property

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago
8.6/10 Excellent! (2,153 reviews)

Jun 15 - Jun 18

3 night stay

Boston (BOS) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
The garage was dark and dengue. The room description said city view. All you could see is a block wall. Orbitz description said the hotel had room service. They don’t. Web Site said no charge for early check in. They charged us $25 The room walls must be thin. We heard people talking from other rooms and in the hall. Anytime a neighbor used the restroom we could hear the water. Basically we got no sleep.

Reviewed on Apr 7, 2024

Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

Downtown Chicago
7.6/10 Good! (6,529 reviews)

Jun 15 - Jun 18

3 night stay

Boston (BOS) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
Very nice rooms and great service

Reviewed on Mar 28, 2024

Prices and availability subject to change. Additional terms may apply.

Top rated hotels for your Southwest Wisconsin vacation package

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
Free Cancellation
Reserve now, pay when you stay
41.95 mi from city center
The price is $129 per night
$129
per night
Apr 25 - Apr 26
Guests of The Madison Concourse Hotel and Governor's Club have access to an indoor pool, a gym, and a sauna. If you drive, self parking is USD 18 per night, or you can take advantage of the free airport shuttle (available on request). Front-desk staff can answer questions 24/7, and assist with concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this luxury hotel include free WiFi in public areas, a spa tub, and a conference center.
Hot Tub
Pet friendly
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Free Cancellation
Reserve now, pay when you stay
16.92 mi from city center
The price is $25 per night
$25
per night
Apr 24 - Apr 25
At Mt. Olympus Water & Theme Park Resort, guests enjoy a free water park, a lazy river, and a children's pool. Self parking is offered for USD 0.01 per day. The front desk is staffed 24 hours a day to help with access to locker space and tours/tickets. Other amenities at this family-friendly resort include a seasonal outdoor pool, an arcade/game room, and express check-out.
Pool
Parking available
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue, Madison, WI
Free Cancellation
Reserve now, pay when you stay
40.5 mi from city center
The price is $144 per night
$144
per night
May 4 - May 5
Guests of Best Western Plus InnTowner Madison have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking and a free area shuttle. The front desk has multilingual staff on hand 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a spa tub, meeting rooms, and conference space.
Hot Tub
Pool
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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.

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