Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Le Méridien Essex Chicago
Price was $412, price is now $284 per person
$284
per person
Jan 22 - Jan 24
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, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on Nov 3, 2026

Sheraton Grand Chicago Riverwalk
Price was $1,720, price is now $621 per person
$621
per person
Dec 8 - Dec 13
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.

Hotel Riu Plaza Chicago
Price was $1,007, price is now $629 per person
$629
per person
Dec 8 - Dec 13
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.

Level Chicago Fulton Market
Price was $857, price is now $557 per person
$557
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen
Reviewed on Nov 6, 2026

Park Hyatt Chicago
Price was $1,825, price is now $1,236 per person
$1,236
per person
Dec 10 - Dec 13
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.
Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott.
For example, there was a hair in the bed. When we reported it, the hotel changed the sheets and asked if we wanted to switch rooms, but no apology or other compensation was offered.
The service was fine but incredibly slow, which we experienced with three different requests. Two were for the same bath salts, which are already provided in the room, so it wasn’t a special request. We had to call twice, and they arrived after 45 to 55 minutes. For the third, I went down to the front desk to ask for a printer, and they offered to print the documents and send them to my room. After 45 minutes, I went back down, and it turned out they had completely forgotten about the request, so I had them printed right there.
The pool was dirty. On three different occasions over two days, there were toys left in the pool even after the people using them were already gone. The fruit in the gym was also old and had gone bad.
Reviewed on Nov 4, 2026

LondonHouse Chicago, Curio Collection by Hilton
Price was $1,135, price is now $774 per person
$774
per person
Dec 8 - Dec 13
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 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The staff was excellent! The views were amazing and the rooms were clean. The rooftop restaurant/ bar 🎇
Reviewed on Nov 7, 2026

Eurostars Magnificent Mile
Price was $552, price is now $377 per person
$377
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
The room itself was pretty clean, it had a good shower which is sometimes rare to find. The staff was friendly and housekeeping was responsive. Close to things, but I wouldn’t necessarily say walking distance. It was pretty noisy but hard to get away from that in a city.
Reviewed on Nov 7, 2026

Hotel Felix River North/Magnificent Mile
Price was $542, price is now $371 per person
$371
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
This boutique hotel is located in a great area. Our main complaint is the hotel is old and therefore it’s not insulated from noise. We could hear every conversation, siren and party that went on in the streets. Our neighbor was a big snorer so that wasn’t pleasant. Our original room was just outside the elevator, which I did not like but the staff quickly moved us to another room, so that was great. Other than that we enjoyed our stay for the convenience. Lots of great restaurants within walking distance, stores etc.
Reviewed on Nov 5, 2026
Chicago Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Chicago 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, Dec 15 - Tue, Jan 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 3 hours ago
$108
Roundtrip
found 3 hours ago

Tue, Dec 15 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 4 hours ago
$120
Roundtrip
found 4 hours ago

Tue, Jan 19 - Wed, Feb 10
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$128 Roundtrip, found 1 hour ago
$128
Roundtrip
found 1 hour ago

Wed, Dec 30 - Wed, Jan 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Discover Other Travel Deals
- Naval Station Great Lakes Vacations
- Wrigley Field Vacations
- McCormick Place Vacations
- Navy Pier Vacations
- Soldier Field Vacations
- Millennium Park Vacations
- Chicago Riverwalk Vacations
- Six Flags Great America Vacations
- United Center Vacations
- Michigan Avenue Vacations
- Grant Park Vacations
- Lake Michigan 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



