
Cheap Holidays to Southwest Wisconsin
- Top deals for trips to Southwest Wisconsin
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top deals for trips to Southwest Wisconsin
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Hotel Felix River North/Magnificent Mile's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a 24-hour gym and a bar.

4.0-star property
Level Chicago - River North
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
per person
found 23 hours ago
Our customers tell us that they can't get enough of the helpful staff at Level Chicago - River North. During your stay, you're just a quick walk from Merchandise Mart. Enjoy features like free WiFi in public areas, plus a gym and concierge services. This property offers pet-friendly amenities, such as an off-lead area.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Hilton Chicago
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Our customers tell us they can't get enough of Hilton Chicago's great location. During your stay, you're just a quick walk from Art Institute of Chicago. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
Southwest Wisconsin Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Hotel Felix River North/Magnificent Mile's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a 24-hour gym and a bar.

4.0-star property
Level Chicago - River North
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
per person
found 23 hours ago
Our customers tell us that they can't get enough of the helpful staff at Level Chicago - River North. During your stay, you're just a quick walk from Merchandise Mart. Enjoy features like free WiFi in public areas, plus a gym and concierge services. This property offers pet-friendly amenities, such as an off-lead area.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Hilton Chicago
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Our customers tell us they can't get enough of Hilton Chicago's great location. During your stay, you're just a quick walk from Art Institute of Chicago. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 23 hours ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
Best Southwest Wisconsin hotel deals for your holiday

Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road, Wisconsin Dells, WI
The price is €86 per night
€86
6 Jul - 7 Jul
includes taxes & fees
27.24 km from city centre
Mt. Olympus Water & Theme Park Resort's good location gets good marks from our customers. During your stay, you're just a quick walk from Paul Bunyan's Northwoods Lumberjack Show. Enjoy features like a restaurant, a bar and a coffee shop/cafe.
Uima-allas
Ravintola

The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
67.55 km from city centre
The breakfast at The Madison Concourse Hotel and Governor's Club gets high marks from our customers. During your stay, you're just a quick walk from Capitol Square. Features include free WiFi in public areas and a free round-trip airport shuttle, plus an indoor pool.
Uima-allas
Poreallas

Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
The price is €62 per night
€62
14 Jul - 15 Jul
includes taxes & fees
59.07 km from city centre
Our customers tell us that they can't get enough of the free breakfast at Baymont by Wyndham Madison West/Middleton WI West. During your stay, you'll be within walking distance of Walnut Grove Dog Park. Free WiFi in public areas, free self-parking and a free round-trip airport shuttle are available.
Uima-allas
Poreallas

Natura Treescape Resort
400 County Road A, Wisconsin Dells, WI
27.59 km from city centre
Our customers tell us that they can't get enough of the pool at Natura Treescape Resort. During your stay, you're just a quick walk from Mt. Olympus Water and Theme Park. Enjoy features like free WiFi in public areas, plus 2 indoor pools and a restaurant.

Atlantis Family Waterpark Hotel, Ascend Hotel Collection
1570 Wisconsin Dells Pkwy, Wisconsin Dells, WI
The price is €105 per night
€105
6 Jul - 7 Jul
includes taxes & fees
26.31 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Atlantis Family Waterpark Hotel, Ascend Hotel Collection. During your stay, you're just a quick walk from Noah's Ark Waterpark. You'll find features such as free WiFi in public areas and free self-parking, plus 3 indoor pools.
Uima-allas
Poreallas

Days Inn & Suites by Wyndham Wisconsin Dells
2504 Wisconsin Dells Parkway, Wisconsin Dells, WI
The price is €60 per night
€60
20 Jul - 21 Jul
includes taxes & fees
28.08 km from city centre
Our customers tell us they can't get enough of Days Inn & Suites by Wyndham Wisconsin Dells's great location. During your stay, you're just a quick walk from Vertical Illusions. Free breakfast, free WiFi in public areas and free self-parking are available.
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View all propertiesLowest 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.
Cheap flights to Southwest Wisconsin
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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^Savings based on all package bookings with Flight + Hotel made on ebookers.fi from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.