Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $402, price is now $269 per person
$269
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Good location, small rooms, they charge for use of an umbrella and no cups in room. In their lobby they have a bar and fireplace and I like that.
Reviewed on Oct 19, 2026
Swissotel - Chicago
Save 100% on your flight
Price was $625, price is now $382 per person
$382
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
It was a great location
Reviewed on Oct 18, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $567, price is now $348 per person
$348
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
My husband and I loved the large shower booth and comfy bed. Also the room was very quiet so we were able to have a quality sleep at night. The breakfast buffet was very nice too, lots of different dishes and they were tasty! Would definitely come back.
(Only one thing I did not like was a strong scent at the lobby area. Maybe tone it down a little bit?)
Reviewed on Oct 18, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $720, price is now $448 per person
$448
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Save 100% on your flight
Price was $861, price is now $546 per person
$546
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pendry Chicago
Save 100% on your flight
Price was $941, price is now $609 per person
$609
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Staff was friendly and polite. In-room dining set a high bar both in quality and service.
Reviewed on Oct 19, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,106, price is now $733 per person
$733
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Save 100% on your flight
Price was $420, price is now $281 per person
$281
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Southwest Wisconsin Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Southwest Wisconsin Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Nov 11 - Sat, Nov 14
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Tue, Oct 20 - Tue, Oct 27
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$291 Roundtrip, found 21 hours ago
$291
Roundtrip
found 21 hours ago
Sat, Nov 14 - Tue, Nov 17
BOS
Logan Intl.
MSN
Dane County Regional
$294 Roundtrip, found 12 hours ago
$294
Roundtrip
found 12 hours ago
Mon, Nov 2 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$297 Roundtrip, found 8 hours ago
$297
Roundtrip
found 8 hours ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
- Nearby Destinations
- Areas of Southwest Wisconsin
- Hotwire Picks
- Kalahari Indoor Waterpark Vacations
- University of Wisconsin-Madison Vacations
- Noah's Ark Waterpark Vacations
- Chula Vista Waterparks Vacations
- Alliant Energy Center Vacations
- Camp Randall Stadium Vacations
- Mt. Olympus Water and Theme Park Vacations
- East Towne Mall Vacations
- Devil's Lake State Park Vacations
- La Crosse Center Vacations
- Christmas Mountain Vacations
- University of Wisconsin-La Crosse Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
