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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $719, price is now $484 per person
$484
per person
Jul 9 - Jul 12
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $793, price is now $503 per person
$503
per person
Jun 14 - Jun 17
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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Save 100% on your flight
Price was $817, price is now $537 per person
$537
per person
Jul 9 - Jul 12
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 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $854, price is now $571 per person
$571
per person
Jul 1 - Jul 6
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Save 100% on your flight
Price was $872, price is now $585 per person
$585
per person
Jul 1 - Jul 6
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,823, price is now $1,231 per person
$1,231
per person
Jul 1 - Jul 5
found 24 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.
Fenway House Hotel

Fenway House Hotel

2.5 out of 5
Price was $742, price is now $503 per person
$503
per person
Jun 3 - Jun 10
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Madison (MSN)
Stay at this hotel in Fennimore. Enjoy free WiFi, a 24-hour front desk, and a conference center. Popular attractions Fennimore Railroad Historical Society Museum and Fennimore Doll and Toy Museum are located nearby.
Lodge Geneva National

Lodge Geneva National

4 out of 5
Save 100% on your flight
Price was $1,159, price is now $787 per person
$787
per person
Jul 2 - Jul 6
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Geneva Lake and Geneva National Golf Club are located nearby.

Southwest Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $626, price is now $406 per person
$406
per person
Jul 2 - Jul 5
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,020, price is now $605 per person
$605
per person
Jun 17 - Jun 21
found 1 day 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 $793, price is now $503 per person
$503
per person
Jun 14 - Jun 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $817, price is now $537 per person
$537
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $827, price is now $483 per person
$483
per person
Jul 1 - Jul 6
found 20 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 $1,769, price is now $984 per person
$984
per person
Jun 10 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,284, price is now $1,302 per person
$1,302
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,000, price is now $1,181 per person
$1,181
per person
Jun 9 - Jun 16
found 1 day 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.

Frontier Airlines
Thu, May 14 - Sun, May 17
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$164 Roundtrip, found 10 hours ago
$164
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Thu, May 14 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Sun, May 17, priced at $164 found 10 hours ago
American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$167 Roundtrip, found 17 hours ago
$167
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $167 found 17 hours ago
Frontier Airlines
Sun, May 17 - Sat, May 23
LAX
Los Angeles Intl.
MSN
Dane County Regional
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, May 17 from Los Angeles Intl. to Dane County Regional, returning Sat, May 23, priced at $190 found 6 days ago
Frontier Airlines
Sat, May 30 - Tue, Jun 9
DEN
Denver Intl.
MSN
Dane County Regional
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 30 from Denver Intl. to Dane County Regional, returning Tue, Jun 9, priced at $213 found 1 day ago