Des Plaines Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Des Plaines Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $725, price is now $511 per person
$511
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
wonderful staff
Reviewed on Jul 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,010, price is now $619 per person
$619
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The property was amazing including the buffet breakfast.
Reviewed on Jul 6, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,267, price is now $789 per person
$789
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,208, price is now $799 per person
$799
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Great boutique hotel in a great location! Definitely will stay here again when visiting Chicago.
Reviewed on Jul 5, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,096, price is now $747 per person
$747
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Amazing hotel and you can't beat the Navy Pier location.
Reviewed on Jul 5, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,139, price is now $784 per person
$784
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Great location. Well maintained hotel. I would highly recommend.
Reviewed on Jul 5, 2026
Don't see what you're looking for?
See all available trips from Columbus to Des Plaines
View all tripsDes 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 4787 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
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 ...
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 ...
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
26.35 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
6.43 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
6.14 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
26.22 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
26.54 km from city center
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 ...
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
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 ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
26.65 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
27.71 km from city center
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 ...
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
27.15 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
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 ...
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.
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 6 hours ago
$216
Roundtrip
found 6 hours ago
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$256 Roundtrip, found 6 hours ago
$256
Roundtrip
found 6 hours ago
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$266 Roundtrip, found 6 hours ago
$266
Roundtrip
found 6 hours ago
Tue, Aug 11 - Sat, Aug 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$286 Roundtrip, found 3 days ago
$286
Roundtrip
found 3 days ago
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$295 Roundtrip, found 6 hours ago
$295
Roundtrip
found 6 hours ago