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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,200, price is now $717 per person
$717
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms 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 $1,673, price is now $927 per person
$927
per person
Aug 22 - Aug 28
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

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $2,105, price is now $1,280 per person
$1,280
per person
Aug 22 - Aug 28
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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,162, price is now $750 per person
$750
per person
Sep 3 - Sep 8
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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,261, price is now $828 per person
$828
per person
Aug 22 - Aug 28
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,598, price is now $1,058 per person
$1,058
per person
Aug 22 - Aug 28
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 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,215, price is now $814 per person
$814
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Southwest Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $669, price is now $442 per person
$442
per person
Sep 10 - Sep 13
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 $889, price is now $575 per person
$575
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,123, price is now $749 per person
$749
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,014, price is now $580 per person
$580
per person
Sep 3 - Sep 8
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 $1,519, price is now $814 per person
$814
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,003, price is now $589 per person
$589
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,175, price is now $699 per person
$699
per person
Sep 3 - Sep 8
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.

American Airlines
Wed, Jul 1 - Wed, Aug 5
BOS
Logan Intl.
RFD
Greater Rockford
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 1 from Logan Intl. to Greater Rockford, returning Wed, Aug 5, priced at $217 found 1 day ago
Frontier Airlines
Sat, Oct 10 - Sat, Oct 24
DEN
Denver Intl.
MSN
Dane County Regional
$253 Roundtrip, found 4 days ago
$253
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Denver Intl. to Dane County Regional, returning Sat, Oct 24, priced at $253 found 4 days ago
Bargain Flight
Sat, Nov 14 - Mon, Nov 16
BOS
Logan Intl.
MSN
Dane County Regional
$259 Roundtrip, found 9 hours ago
$259
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Sat, Nov 14 from Logan Intl. to Dane County Regional, returning Mon, Nov 16, priced at $259 found 9 hours ago
Bargain Flight
Tue, Aug 4 - Tue, Aug 11
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$266 Roundtrip, found 2 days ago
$266
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Dane County Regional, returning Tue, Aug 11, priced at $266 found 2 days ago