Search Deals on
Southwest Wisconsin Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

A stone viewing platform overlooking a river with a forested hillside in the background.

Southwest Wisconsin
Wisconsin
United States of America
North America
Hotwire.com

Southwest Wisconsin Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Riverview Inn & Suites, an Ascend Collection Hotel

3 out of 5

Save 100% on your flight

Price was $418, price is now $295 per person

$295

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip flight included

Houston (HOU) to Chicago (ORD)

Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Boylan Tennis Center and Anderson Japanese Gardens are located nearby.

Staff were very friendly and helpful. Room had no issues.

Reviewed on Aug 25, 2026

Level Chicago – Old Town

4 out of 5

Save 100% on your flight

Price was $1,087, price is now $641 per person

$641

per person

Nov 5 - Nov 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.

The Emily Hotel

4 out of 5

Save 100% on your flight

Price was $1,624, price is now $1,028 per person

$1,028

per person

Oct 28 - Nov 3

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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5

Save 100% on your flight

Price was $589, price is now $406 per person

$406

per person

Nov 13 - Nov 16

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

4.5 out of 5

Save 100% on your flight

Price was $665, price is now $462 per person

$462

per person

Nov 13 - Nov 16

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.

Great place, friendly/helpful staff, clean/nice rooms (although not a lot of insulation between rooms), good location to parks, museums, and shopping.

Reviewed on Aug 26, 2026

Sentral Michigan Avenue

4 out of 5

Save 100% on your flight

Price was $1,185, price is now $827 per person

$827

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.

Pool was closed both days I stayed

Reviewed on Aug 24, 2026

Hotel Riu Plaza Chicago

4 out of 5

Save 100% on your flight

Price was $1,446, price is now $1,016 per person

$1,016

per person

Oct 22 - Oct 25

found 2 hours ago

Roundtrip flight included

Albuquerque (ABQ) 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.

❤️

Reviewed on Aug 26, 2026

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5

Save 100% on your flight

Price was $1,437, price is now $1,020 per person

$1,020

per person

Oct 27 - Nov 3

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 breakfast and the pool 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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5

Downtown Chicago

Save 100% on your flight

Price was $589, price is now $406 per person

$406

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)