Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Saint Clair- Magnificent Mile
Price was $787, price is now $540 per person
$540
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Clean room
Reviewed on Nov 15, 2026

Hotel Riu Plaza Chicago
Price was $1,571, price is now $887 per person
$887
per person
Dec 26 - Jan 2
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.
Top notch hotel. Never stayed at a Riu property before, but will definitely look into one whenever I am out of town. Clean, modern, and spacious rooms, terrific customer service and the breakfast buffet was very good too.
Reviewed on Nov 15, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Price was $983, price is now $579 per person
$579
per person
Dec 26 - Jan 2
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.
A
Reviewed on Nov 12, 2026

Eurostars Magnificent Mile
Price was $1,349, price is now $826 per person
$826
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel Felix River North/Magnificent Mile
Price was $850, price is now $546 per person
$546
per person
Dec 26 - Jan 2
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.
The room was not ready upon arrival so we had to wait 45 min after check in to get into our room. Additionally, we left the room at 930a , returned at 6p and the room had not been cleaned. There were fresh towels laid on top of the bed but nothing else had been touched. Seemed a little disorganized bc when we asked why the room had been left untouched they said “they were just really busy bc they were booked” but idk, if I’m paying to stay there, it’s not my job to make sure you can handle the level of occupancy you booked. It’s pretty centrally located but I wouldn’t stay here again
Reviewed on Nov 15, 2026

L7 Chicago by LOTTE
Price was $1,487, price is now $989 per person
$989
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Blackstone, Autograph Collection
Price was $966, price is now $657 per person
$657
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Swissotel - Chicago
Price was $1,179, price is now $804 per person
$804
per person
Dec 26 - Jan 2
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.
Beautiful building Nice room sweet customer services. The no microwave and charging customers to warm their food is honestly insane and inconsiderate. It was a 5/10 probably will not be a returning customer.
Reviewed on Nov 15, 2026
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.

Mon, Jan 4 - Sat, Jan 16
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$228 Roundtrip, found 5 hours ago
$228
Roundtrip
found 5 hours ago

Tue, Dec 15 - Sun, Dec 20
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$245 Roundtrip, found 16 hours ago
$245
Roundtrip
found 16 hours ago

Fri, Mar 5 - Tue, Mar 9
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$264 Roundtrip, found 4 hours ago
$264
Roundtrip
found 4 hours ago

Wed, Nov 18 - Fri, Nov 20
DCA
Ronald Reagan Washington National
EAU
Chippewa Valley Regional
$288 Roundtrip, found 6 days ago
$288
Roundtrip
found 6 days ago
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