Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Price was $417, price is now $293 per person
$293
per person
Jan 15 - Jan 18
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, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Wonderful staff!! Welcoming, friendly, and very helpful. We ended up arriving 2 hours before check-in, but staff had no problem helping us out and letting us get our room early. Valet staff hepful when we needed to get an item from the car, James was so awesome helping with luggage and to our room. Housekeeping checked in to see if we were happy with the room, which was very clean!! Each contact we had with staff was a positive one. Lobby was small but cute and eclectic. Wish there was a microwave in the room, but not a deal killer..! Stayed on a Thursday night, seemed like a lot of people checking in and busy, but it was quiet and we slept well. location isn’t overly close to shops, but if you cross Michigan Ave, Grant Park area is right there. You could walk to Art Institute, but I would say wear some good shoes! All in all, would stay again!
Reviewed on Nov 14, 2026
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.
Hotel Saint Clair- Magnificent Mile
Price was $448, price is now $308 per person
$308
per person
Jan 15 - Jan 18
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.
Loved staying here! Beautiful property! Lovely room and amenities! Can’t wait to start again!!
Reviewed on Nov 15, 2026
Hotel Riu Plaza Chicago
Price was $502, price is now $347 per person
$347
per person
Jan 28 - Jan 31
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Price was $886, price is now $628 per person
$628
per person
Jan 28 - Jan 31
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, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Eurostars Magnificent Mile
Price was $475, price is now $338 per person
$338
per person
Jan 15 - Jan 18
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.
Pendry Chicago
Price was $966, price is now $693 per person
$693
per person
Dec 23 - Dec 27
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.
Sheraton Grand Chicago Riverwalk
Price was $701, price is now $509 per person
$509
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue 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.
Mon, Jan 4 - Sat, Jan 16
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$228 Roundtrip, found 19 hours ago
$228
Roundtrip
found 19 hours ago
Tue, Dec 15 - Sun, Dec 20
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$245 Roundtrip, found 8 hours ago
$245
Roundtrip
found 8 hours ago
Fri, Mar 5 - Tue, Mar 9
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$264 Roundtrip, just found
$264
Roundtrip
just found
Wed, Nov 18 - Fri, Nov 20
DCA
Ronald Reagan Washington National
EAU
Chippewa Valley Regional
$288 Roundtrip, found 5 days ago
$288
Roundtrip
found 5 days ago
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