Crestwood Vacations
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Crestwood Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$653
per person
Nov 3 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$897
per person
Nov 3 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Breakfast had some cold cuts, but for a vegan there wasn't much more options than your standard US continental. The TV (which turns on automatically every time you enter the room - very annoying) was the worst setup I've seen in a hotel, the connection to cast wasn't working because the TV wasn't connected to wifi, the remote was weird (no volume/channel controls). Lobby was nauseatingly over-fragranced, makes me wonder what horrible scent they're trying to cover up. Tried to use the stairs instead of the slow elevators and couldn't get out on the 2nd floor for breakfast since the stair exits are locked.
Overall fair to ok but missing the attention to detail that would've been nice at the price point. I definitely wouldn't stay for business travel.
Reviewed on Sep 9, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,470
per person
Nov 3 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago Fulton Market
Downtown Chicago
$1,111
per person
Nov 3 - Nov 8
found 6 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
The pool & jacuzzi was perfect, this hotel is beautiful
Reviewed on Sep 7, 2026
The Talbott, Autograph Collection
Downtown Chicago
$967
per person
Nov 3 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this luxury 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.
Old,
Reviewed on Sep 8, 2026
Level Chicago – Old Town
Downtown Chicago
$958
per person
Nov 3 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Location and facility was very nice
Reviewed on Sep 7, 2026
Crestwood Vacation Packages
Looking for ways save some money and some time on your next trip to Crestwood? The AARP Travel Center Powered by Expedia® can help you do both. 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 Crestwood the best one yet. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. AARP Travel Center has an incredible choice of accommodations and flight, as well as local activities to pull from.
Crestwood Hotels
With 3637 hotels and resorts in Crestwood to choose from, you are bound to find one that meets your needs.
From Crestwood hotels with multiple pools and on-site restaurants, to boutique accommodations that add all the thoughtful touches, you'll find a hotel here that will make your trip amazing. With AARP Travel Center's Crestwood hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Crestwood
Crestwood has about 10,984 people that call this city their home. If you wanted to take a break from the fast pace of a big city, then you are in the right spot. With Crestwood's growing artistry scene and plenty of interest for history buffs you may have a hard time fitting everything into one trip.
You can also check out our "Things to Do" page for more inspiration or to book an activity in Crestwood.
Package Your Crestwood Vacation and Save
As an AARP Member, you get to benefit from all the great deals. You'll save on select hotels worldwide, flights, and also car rentals. No matter what Crestwood vacation package you select, you can rest easy knowing that you already saved on your trip. The hardest packing you'll have to do is for your suitcase. Book today and get ready for your Crestwood vacation.
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
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 ...
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
River Hotel
75 East Wacker Drive Chicago IL
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 ...
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
Hilton Chicago
720 S Michigan Ave Chicago IL
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 ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
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 ...
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
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 Wade
644 N Lake Shore Dr Chicago IL
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 ...
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
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 ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
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 ...
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
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 ...
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.
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 2 days ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 2 days ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237
Roundtrip
found 2 days ago
Fri, Oct 2 - Mon, Oct 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$237
Roundtrip
found 4 days ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$272
Roundtrip
found 2 days ago
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All accommodation types in Crestwood
More Types of Hotels
- Hotels with Bars in Crestwood
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- Cheap Hotels in Crestwood
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- Hotels with Complimentary Breakfast in Crestwood
- Smoke Free Hotels in Crestwood
- Hotels with an Indoor Pool in Crestwood
- Hotel with wifi in Crestwood
- Hotels with Air Conditioning in Crestwood