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

Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $564, price is now $370 per person
$370
per person
Jan 13 - Jan 17
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.
Great location with good walkability to the train.
Reviewed on Nov 6, 2026

Sheraton Grand Chicago Riverwalk
Save 100% on your flight
Price was $1,052, price is now $571 per person
$571
per person
Dec 18 - Dec 22
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 MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Save 100% on your flight
Price was $590, price is now $375 per person
$375
per person
Jan 13 - Jan 17
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.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $686, price is now $445 per person
$445
per person
Jan 13 - Jan 17
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.

Pendry Chicago
Save 100% on your flight
Price was $617, price is now $415 per person
$415
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.
Beautiful rooms and service.
Reviewed on Nov 5, 2026

Level Chicago Fulton Market
Price was $931, price is now $630 per person
$630
per person
Dec 28 - Jan 1
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

Park Hyatt Chicago
Price was $1,825, price is now $1,236 per person
$1,236
per person
Dec 10 - Dec 13
found 5 hours 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

Level Chicago – Old Town
Price was $733, price is now $498 per person
$498
per person
Jan 22 - Jan 25
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.
Lakeside Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Lakeside 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.

Fri, Dec 4 - Wed, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$186 Roundtrip, found 3 hours ago
$186
Roundtrip
found 3 hours ago

Wed, Dec 2 - Fri, Dec 4
LAX
Los Angeles Intl.
MDW
Midway Intl.
$238 Roundtrip, found 5 hours ago
$238
Roundtrip
found 5 hours ago

Sat, Nov 7 - Thu, Nov 12
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago

Thu, Nov 12 - Mon, Nov 23
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,139 Roundtrip, just found
$1,139
Roundtrip
just found
Discover Other Travel Deals
- Lake Michigan Vacations
- Indiana Dunes National Park Vacations
- Four Winds Casino New Buffalo Vacations
- Silver Beach Vacations
- Blue Chip Casino Vacations
- Warren Dunes State Park Vacations
- New Buffalo Public Beach Vacations
- Lighthouse Place Premium Outlets Vacations
- Andrews University Vacations
- Round Barn Winery Vacations
- Washington Park Zoo 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


