Search Deals onSoutheast Wisconsin Vacation Packages
Southeast Wisconsin Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Price was $533, price is now $340 per person
$340
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Roman everything was clean everything was made that was all and it was very
Reviewed on Nov 4, 2026

Sheraton Grand Chicago Riverwalk
Price was $1,482, price is now $470 per person
$470
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Emily Hotel
Save 100% on your flight
Price was $830, price is now $507 per person
$507
per person
Dec 24 - Dec 29
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.
Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!
Reviewed on Nov 4, 2026

Level Chicago Fulton Market
Save 100% on your flight
Price was $639, price is now $403 per person
$403
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa.
There was no housekeeping.
Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before you arrive!
There is no lobby, no where in the hotel to hang, no vibe. You are literally staying in a condo and have to exit the building and walk a few blocks to be anywhere. Maybe this is the new hotel experience, but for me, I still like some ammenities.
The room was fine
T
Reviewed on Nov 4, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Price was $1,108, price is now $704 per person
$704
per person
Dec 16 - Dec 23
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.

Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $735, price is now $469 per person
$469
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Hotel Saint Clair- Magnificent Mile
Price was $541, price is now $349 per person
$349
per person
Jan 15 - Jan 19
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.
Elevator was slow but everything else was great!
Reviewed on Nov 4, 2026

Pendry Chicago
Price was $599, price is now $400 per person
$400
per person
Dec 16 - Dec 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 rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
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.

Tue, Nov 24 - Mon, Dec 7
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$123 Roundtrip, found 7 hours ago
$123
Roundtrip
found 7 hours ago

Thu, Nov 12 - Sun, Nov 22
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$206 Roundtrip, found 1 hour ago
$206
Roundtrip
found 1 hour ago
Thu, Dec 17 - Thu, Dec 24
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$208 Roundtrip, found 11 hours ago
$208
Roundtrip
found 11 hours ago

Fri, Dec 25 - Thu, Jan 14
DEN
Denver Intl.
MKE
General Mitchell Intl.
$228 Roundtrip, found 4 hours ago
$228
Roundtrip
found 4 hours ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
- Nearby Destinations
- Areas of Southeast Wisconsin
- Hotwire Picks
- Lake Michigan Vacations
- American Family Field Vacations
- Fiserv Forum Vacations
- Baird Center Vacations
- Geneva Lake Vacations
- University of Wisconsin-Milwaukee Vacations
- Marquette University Vacations
- Harley-Davidson Museum Vacations
- The Rave-Eagles Club Vacations
- Milwaukee County Zoo Vacations
- Mayfair Mall Vacations
- Potawatomi Bingo Casino 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


