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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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,064, price is now $727 per person
$727
per person
Jul 8 - Jul 11
found 10 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,288, price is now $1,400 per person
$1,400
per person
Jul 31 - Aug 3
found 6 hours ago
Roundtrip flight included
Mesa (AZA) 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $2,434, price is now $1,501 per person
$1,501
per person
Jul 2 - Jul 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,740, price is now $1,114 per person
$1,114
per person
Jul 31 - Aug 3
found 6 hours ago
Roundtrip flight included
Mesa (AZA) 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

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,998, price is now $1,331 per person
$1,331
per person
Jul 31 - Aug 3
found 6 hours ago
Roundtrip flight included
Mesa (AZA) 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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,227, price is now $1,520 per person
$1,520
per person
Jul 29 - Aug 3
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff 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 $2,167, price is now $1,483 per person
$1,483
per person
Jul 29 - Aug 3
found 21 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Lodge Geneva National

Lodge Geneva National

4 out of 5
Save 100% on your flight
Price was $1,598, price is now $1,102 per person
$1,102
per person
Jun 23 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
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 $843, price is now $513 per person
$513
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,288, price is now $1,400 per person
$1,400
per person
Jul 31 - Aug 3
found 6 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,740, price is now $1,114 per person
$1,114
per person
Jul 31 - Aug 3
found 6 hours ago
Roundtrip flight included
Mesa (AZA) 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 $1,998, price is now $1,331 per person
$1,331
per person
Jul 31 - Aug 3
found 6 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)

Southwest Wisconsin Vacation Packages 5-7 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 $1,104, price is now $687 per person
$687
per person
Jul 2 - Jul 7
found 1 hour ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,047, price is now $1,644 per person
$1,644
per person
Jul 29 - Aug 3
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,528, price is now $1,428 per person
$1,428
per person
Jul 29 - Aug 3
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,186, price is now $1,338 per person
$1,338
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Phoenix (PHX) 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, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$201 Roundtrip, found 7 hours ago
$201
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $201 found 7 hours ago
Bargain Flight
Tue, Jul 28 - Tue, Aug 11
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Tue, Jul 28 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Tue, Aug 11, priced at $204 found 5 days ago
Frontier Airlines
Tue, Jul 14 - Tue, Jul 28
DEN
Denver Intl.
MSN
Dane County Regional
$218 Roundtrip, found 7 hours ago
$218
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Denver Intl. to Dane County Regional, returning Tue, Jul 28, priced at $218 found 7 hours ago
Bargain Flight
Tue, May 26 - Sun, May 31
MSP
Minneapolis - St. Paul Intl.
ATW
Appleton Intl.
$233 Roundtrip, found 6 days ago
$233
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Tue, May 26 from Minneapolis - St. Paul Intl. to Appleton Intl., returning Sun, May 31, priced at $233 found 6 days ago