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
Save 100% on your flight
Price was $544, price is now $370 per person
$370
per person
Sep 11 - Sep 13
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.
Room was clean and close to everything
Reviewed on Aug 4, 2026
Four Seasons Hotel Chicago
Price was $4,688, price is now $2,724 per person
$2,724
per person
Sep 13 - Sep 19
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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Yes
Reviewed on Aug 3, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,563, price is now $928 per person
$928
per person
Oct 21 - Oct 25
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.
Perfect
Reviewed on Aug 4, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $983, price is now $628 per person
$628
per person
Oct 22 - Oct 25
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.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $1,103, price is now $706 per person
$706
per person
Sep 4 - Sep 8
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 Emily Hotel
Save 100% on your flight
Price was $1,453, price is now $962 per person
$962
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.
This was a family trip, so maybe not the right location. There was a LOT of construction in the area. There was no parking for hotel guests, unless you paid over $80 a day for valet only. The space was very modern, but dark. The beds were low to the ground and uncomfortable. Clean, but minimal accommodations. Staff was minimally helpful with questions we had. We won’t be staying here again.
Reviewed on Aug 4, 2026
The Talbott, Autograph Collection
Save 100% on your flight
Price was $753, price is now $510 per person
$510
per person
Oct 22 - Oct 25
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 Michigan Avenue and Chicago Riverwalk are located nearby.
The hotel is in an older building, but they have done a great job adding modern amenities. The bar and restaurant leave a bit to be desired but the decor is nice and the service is helpful.
Reviewed on Aug 3, 2026
Villa Christina
Save 100% on your flight
Price was $751, price is now $511 per person
$511
per person
Oct 8 - Oct 11
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Griffin Museum of Science and Industry and Obama's House are located nearby.
Property was maintained very well, very clean with some artful style. Staff reaponsed quickly fie any needs or inquiry. Feels like a home. Community is safe and neighbors are nice. Street parking is reletively easy.
Reviewed on Aug 4, 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, Nov 9 - Fri, Nov 13
DEN
Denver Intl.
MSN
Dane County Regional
$190 Roundtrip, found 21 hours ago
$190
Roundtrip
found 21 hours ago
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Sat, Nov 14 - Mon, Nov 16
BOS
Logan Intl.
MSN
Dane County Regional
$260 Roundtrip, found 17 hours ago
$260
Roundtrip
found 17 hours ago
Fri, Sep 11 - Fri, Sep 11
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
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