Des Plaines Vacations

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Des Plaines Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
$539
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) 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

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$671
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$798
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
$540
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
The staff was extremely accommodating, it was marathon week so I understand things can be tough, my issues were with the room as a whole. The shower would leak into the bathroom and completely cover the floor and when I informed staff I was having flooding problems they said oh it’s the shower curtain as if it’s a common issue. The wall paper in the bathroom was peeling off the wall. Tv guide didn’t work so you get to play channel roulette. On the plus side staff was great and they provided cold drinks in the morning, ac works really well

Reviewed on Oct 14, 2026

Hotel 505 River North

Hotel 505 River North

Downtown Chicago
$560
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$816
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
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Des Plaines Vacation Packages

Looking to save money and time on your next holiday to Des Plaines? Well, AARP Travel Center Powered by Expedia® is here to help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Des Plaines perfect. In only a few clicks, you can select the best Des Plaines vacation package for you and your family. We have an amazing list of accommodations and flight, and Des Plaines activities to pull from.

Des Plaines Hotels

You can choose from around 4915 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Des Plaines hot spots, we have plenty of options available.

We have great deals on everything from luxury hotels that meet all the vacation must-haves to affordable accommodations perfect for those on looking to save. You can browse our vast catalog of options and select the hotel that is perfect for you and your family. With AARP Travel Center's Des Plaines hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Des Plaines

Des Plaines is larger than it may seem with around 58,677 people calling this city their home. With this area's growing artistry scene and a rich past that is a beacon for history fans you may have a hard time fitting everything into one trip.

If you are looking for more, then head over to our "Things to Do" tab for more inspiration or to reserve an activity in Des Plaines.

Package Your Des Plaines Vacation and Save

With so much to see and do in Des Plaines, you'll be wanting to focus on your itinerary, not spending time to searching for the hotel with the lowest rate. The AARP Travel Center Powered by Expedia® allows you to quickly reserve everything you wish for, and save a little money on your vacation. You can coordinate your whole trip, including things to do in Des Plaines from just one place. The hardest packing you'll have to do is for your suitcase. Bundle today and save!

Top Hotel Deals

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3001 South Mannheim Road Des Plaines IL
3.8 km from city center
Book a stay at this business-friendly hotel in Des Plaines. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
27.71 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
26.75 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL
26.43 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
25.4 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Wade

The Wade

644 N Lake Shore Dr Chicago IL
27.05 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Hilton Chicago

Hilton Chicago

720 S Michigan Ave Chicago IL
27.88 km from city center
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Eurostars Magnificent Mile

Eurostars Magnificent Mile

660 North State Street Chicago IL
26.15 km from city center
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 ...
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL
26.98 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Freehand Chicago

Freehand Chicago

19 East Ohio Street Chicago IL
26.35 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

71 E Wacker Dr Chicago IL
26.77 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

162 East Ontario Street Chicago IL
26.56 km from city center
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 ...
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL
26.99 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

203 N Wabash Ave Chicago IL
26.86 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

127 West Huron, at LaSalle Chicago IL
25.86 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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