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Southwest Wisconsin Vacation Packages

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Southwest Wisconsin Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
Save 100% on your flight
Price was $430, price is now $263 per person
$263
per person
Mar 16 - Mar 21
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Chicago Ridge Shopping Mall and PGN Jump N' Fun Entertainment are located nearby.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $628, price is now $354 per person
$354
per person
Apr 3 - Apr 6
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $730, price is now $428 per person
$428
per person
Apr 1 - Apr 4
found 20 hours 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $703, price is now $430 per person
$430
per person
Apr 4 - Apr 7
found 19 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, 2 bars/lounges, 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $675, price is now $420 per person
$420
per person
Apr 1 - Apr 4
found 20 hours 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,523, price is now $966 per person
$966
per person
Mar 13 - Mar 15
found 17 hours 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.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,764, price is now $1,124 per person
$1,124
per person
Apr 3 - Apr 8
found 12 hours 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.
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $568, price is now $373 per person
$373
per person
Apr 1 - Apr 4
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Southwest Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $628, price is now $354 per person
$354
per person
Apr 3 - Apr 6
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $730, price is now $428 per person
$428
per person
Apr 1 - Apr 4
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,023, price is now $622 per person
$622
per person
Mar 19 - Mar 22
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $703, price is now $430 per person
$430
per person
Apr 4 - Apr 7
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)

Southwest Wisconsin Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $803, price is now $412 per person
$412
per person
Mar 27 - Apr 1
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $856, price is now $471 per person
$471
per person
Mar 27 - Apr 1
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,070, price is now $596 per person
$596
per person
Feb 11 - Feb 18
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $952, price is now $534 per person
$534
per person
Mar 27 - Apr 1
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Tue, Feb 17 - Thu, Feb 19
LAS
Harry Reid Intl.
RFD
Greater Rockford
$193 Roundtrip, found 4 hours ago
$193
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Feb 17 from Harry Reid Intl. to Greater Rockford, returning Thu, Feb 19, priced at $193 found 4 hours ago
Frontier Airlines
Thu, Apr 9 - Sun, Apr 12
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$226 Roundtrip, found 1 hour ago
$226
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Sun, Apr 12, priced at $226 found 1 hour ago
American Airlines
Wed, Mar 25 - Tue, Mar 31
LAS
Harry Reid Intl.
MSN
Dane County Regional
$229 Roundtrip, found 19 hours ago
$229
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Wed, Mar 25 from Harry Reid Intl. to Dane County Regional, returning Tue, Mar 31, priced at $229 found 19 hours ago
Bargain Flight
Fri, Jan 30 - Sun, Feb 1
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$245 Roundtrip, found 2 days ago
$245
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Fri, Jan 30 from Ronald Reagan Washington National to Dane County Regional, returning Sun, Feb 1, priced at $245 found 2 days ago