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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.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $508, price is now $284 per person
$284
per person
Oct 29 - Nov 3
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $1,362, price is now $675 per person
$675
per person
Oct 31 - Nov 5
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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was $2,412, price is now $1,327 per person
$1,327
per person
Oct 31 - Nov 5
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $655, price is now $381 per person
$381
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,055, price is now $617 per person
$617
per person
Nov 10 - Nov 16
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, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Save 100% on your flight
Price was $559, price is now $334 per person
$334
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Lincolnshire. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Marriott Theatre and Valentino Vineyards are located nearby.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Save 100% on your flight
Price was $543, price is now $331 per person
$331
per person
Oct 29 - Nov 3
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Rivers Casino are located nearby.
The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $1,894, price is now $1,159 per person
$1,159
per person
Oct 31 - Nov 5
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Southwest Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Merrillville

Hilton Garden Inn Merrillville

3 out of 5
Green Acres
Save 100% on your flight
Price was $380, price is now $265 per person
$265
per person
Oct 30 - Nov 2
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,151, price is now $739 per person
$739
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
Downtown Kenosha
Save 100% on your flight
Price was $496, price is now $334 per person
$334
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $538 per person
$538
per person
Oct 2 - Oct 6
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,011, price is now $520 per person
$520
per person
Oct 31 - Nov 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
Price was $1,362, price is now $675 per person
$675
per person
Oct 31 - Nov 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 $1,333, price is now $680 per person
$680
per person
Oct 22 - Oct 27
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,080, price is now $1,111 per person
$1,111
per person
Oct 31 - Nov 5
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.

Bargain Flight
Tue, Oct 14 - Wed, Oct 15
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Oct 14 from Ronald Reagan Washington National to Dane County Regional, returning Wed, Oct 15, priced at $218 found 1 day ago
Bargain Flight
Thu, Sep 4 - Fri, Sep 5
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$227 Roundtrip, found 2 days ago
$227
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Thu, Sep 4 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Fri, Sep 5, priced at $227 found 2 days ago
American Airlines
Wed, Dec 24 - Wed, Dec 31
LAS
Harry Reid Intl.
MSN
Dane County Regional
$229 Roundtrip, found 7 hours ago
$229
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Dec 24 from Harry Reid Intl. to Dane County Regional, returning Wed, Dec 31, priced at $229 found 7 hours ago
Frontier Airlines
Sun, Aug 31 - Thu, Sep 4
DEN
Denver Intl.
MSN
Dane County Regional
$241 Roundtrip, found 13 hours ago
$241
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sun, Aug 31 from Denver Intl. to Dane County Regional, returning Thu, Sep 4, priced at $241 found 13 hours ago