Search Deals onSoutheast Wisconsin Vacation Packages
Southeast Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
Save 100% on your flight
Price was $596, price is now $348 per person
$348
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Four Seasons Hotel Chicago
Price was $4,740, price is now $2,744 per person
$2,744
per person
Sep 13 - Sep 19
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Whitehall Hotel, BW Premier Collection
Save 100% on your flight
Price was $991, price is now $600 per person
$600
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The breakfast was very minimal.
Reviewed on Aug 7, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $2,567, price is now $1,584 per person
$1,584
per person
Sep 13 - Sep 19
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,224, price is now $761 per person
$761
per person
Oct 22 - Oct 25
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 Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $731, price is now $456 per person
$456
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
This place showed up in the options for 18+ check-in allowed, but it turns out it wasn't. That might be my fault on my part but it should be made clearer through Expedia. Staff were okay; some were a little rude but not overly. The hotel room itself was clean, and there were no problems in that regard. The stay was expensive due to travelling during Lollapalooza and would most likely be cheaper at any other time. Overall 3/5. Not worth the money, but would be much more worth it if it was cheaper.
Reviewed on Aug 6, 2026
Swissotel - Chicago
Save 100% on your flight
Price was $1,047, price is now $698 per person
$698
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $816, price is now $550 per person
$550
per person
Oct 22 - Oct 25
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.
Great beautiful rooms. Nice beds
Reviewed on Aug 7, 2026
Southeast Wisconsin Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Southeast Wisconsin Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$128 Roundtrip, found 1 hour ago
$128
Roundtrip
found 1 hour ago
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Sat, Aug 15 - Tue, Sep 1
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Mon, Aug 10 - Thu, Aug 27
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
- Nearby Destinations
- Areas of Southeast Wisconsin
- Hotwire Picks
- American Family Field Vacations
- Milwaukee County Zoo Vacations
- Fiserv Forum Vacations
- Harley-Davidson Museum Vacations
- Baird Center Vacations
- Geneva Lake Vacations
- Wisconsin State Fair Park Vacations
- University of Wisconsin-Milwaukee Vacations
- Marquette University Vacations
- Henry W. Maier Festival Park Vacations
- Potawatomi Bingo Casino Vacations
- Mayfair Mall Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
