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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.
Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Save 100% on your flight
Price was $348, price is now $226 per person
$226
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Woodfield Mall and Schaumburg Medieval Times are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,461, price is now $740 per person
$740
per person
May 1 - May 5
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $813, price is now $472 per person
$472
per person
May 1 - May 5
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,234, price is now $721 per person
$721
per person
May 1 - May 5
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,164, price is now $717 per person
$717
per person
May 1 - May 5
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 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center 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 $1,321, price is now $814 per person
$814
per person
May 1 - May 5
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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $876, price is now $552 per person
$552
per person
May 1 - May 5
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.
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $1,032, price is now $654 per person
$654
per person
May 1 - May 5
found 1 day 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.
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 $813, price is now $472 per person
$472
per person
May 1 - May 5
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
Price was $1,461, price is now $740 per person
$740
per person
May 1 - May 5
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 $1,234, price is now $721 per person
$721
per person
May 1 - May 5
found 1 day 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 $1,164, price is now $717 per person
$717
per person
May 1 - May 5
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.
Holiday Inn Aurora North - Naperville by IHG

Holiday Inn Aurora North - Naperville by IHG

3 out of 5
West Aurora
Save 100% on your flight
Price was $420, price is now $297 per person
$297
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,413, price is now $956 per person
$956
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $497, price is now $351 per person
$351
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
SpringHill Suites by Marriott Chicago Southwest at Burr Ridge/Hinsdale

SpringHill Suites by Marriott Chicago Southwest at Burr Ridge/Hinsdale

3 out of 5
Save 100% on your flight
Price was $460, price is now $328 per person
$328
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Fri, Mar 6 - Mon, Mar 9
DEN
Denver Intl.
MSN
Dane County Regional
$115 Roundtrip, found 7 hours ago
$115
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Mar 6 from Denver Intl. to Dane County Regional, returning Mon, Mar 9, priced at $115 found 7 hours ago
United
Wed, Jun 24 - Tue, Jun 30
LAS
Harry Reid Intl.
MSN
Dane County Regional
$229 Roundtrip, found 12 hours ago
$229
Roundtrip
found 12 hours ago
Select United flight, departing Wed, Jun 24 from Harry Reid Intl. to Dane County Regional, returning Tue, Jun 30, priced at $229 found 12 hours ago
Delta
Sat, Aug 8 - Tue, Aug 25
DEN
Denver Intl.
ATW
Appleton Intl.
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 8 from Denver Intl. to Appleton Intl., returning Tue, Aug 25, priced at $229 found 1 day ago
American Airlines
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 17 from Los Angeles Intl. to Greater Rockford, returning Wed, Mar 25, priced at $242 found 1 day ago