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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 $296, price is now $169 per person
$169
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $457, price is now $238 per person
$238
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $1,206, price is now $638 per person
$638
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
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 $996, price is now $535 per person
$535
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Save 100% on your flight
Price was $673, price is now $369 per person
$369
per person
Nov 25 - Dec 2
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 a fitness center. Popular attractions United Center and Chicago Riverwalk are located nearby.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $831, price is now $467 per person
$467
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Save 100% on your flight
Price was $525, price is now $299 per person
$299
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rob Roy Golf Course and Northbrook Sports Complex 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 $296, price is now $169 per person
$169
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $238 per person
$238
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $521, price is now $280 per person
$280
per person
Jan 7 - Jan 11
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 $597, price is now $358 per person
$358
per person
Jan 2 - Jan 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $478 per person
$478
per person
Nov 25 - Dec 2
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,206, price is now $638 per person
$638
per person
Nov 25 - Dec 2
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
Price was $1,225, price is now $651 per person
$651
per person
Nov 25 - Dec 2
found 14 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
Thu, Dec 11 - Mon, Dec 15
LAS
Harry Reid Intl.
RFD
Greater Rockford
$141 Roundtrip, found 3 days ago
$141
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 11 from Harry Reid Intl. to Greater Rockford, returning Mon, Dec 15, priced at $141 found 3 days ago
Bargain Flight
Wed, Dec 3 - Sat, Dec 13
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Wed, Dec 3 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Sat, Dec 13, priced at $189 found 6 days ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$189 Roundtrip, found 6 hours ago
$189
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $189 found 6 hours ago
Frontier Airlines
Fri, Oct 24 - Mon, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Mon, Nov 10, priced at $191 found 1 day ago