Search Deals onSouthwest Wisconsin Vacation Packages
Southwest Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont
Save 100% on your flight
Price was $418, price is now $294 per person
$294
per person
May 18 - May 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
JW Marriott Chicago
Price was $1,247, price is now $624 per person
$624
per person
May 14 - May 18
found 5 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Holiday Inn Chicago – Midway Airport S by IHG
Save 100% on your flight
Price was $959, price is now $635 per person
$635
per person
Jun 5 - Jun 10
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 fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Price was $622, price is now $421 per person
$421
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,293, price is now $879 per person
$879
per person
Jun 18 - Jun 21
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,182, price is now $806 per person
$806
per person
Jun 18 - Jun 21
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.
Fairmont Chicago at Millennium Park
Save 100% on your flight
Price was $1,507, price is now $1,052 per person
$1,052
per person
Jun 15 - Jun 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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hilton Rosemont Chicago O'Hare
Save 100% on your flight
Price was $1,002, price is now $713 per person
$713
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre 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.
Thu, Apr 9 - Mon, Apr 13
BOS
Logan Intl.
RFD
Greater Rockford
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Tue, Jun 9 - Tue, Jun 16
DEN
Denver Intl.
MSN
Dane County Regional
$244 Roundtrip, found 10 hours ago
$244
Roundtrip
found 10 hours ago
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$248 Roundtrip, found 2 hours ago
$248
Roundtrip
found 2 hours ago
Thu, Apr 30 - Sun, May 3
MSP
Minneapolis - St. Paul Intl.
RFD
Greater Rockford
$248 Roundtrip, found 3 hours ago
$248
Roundtrip
found 3 hours ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
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- Areas of Southwest Wisconsin
- Hotwire Picks
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