Crestwood, IL

Travel Guide

A serene lake with reflections of trees and a cloudy sky.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$106 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
Total with taxes and fees
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 ...
8/10 Very Good! (10,177 reviews)
"If you’re going to a bears game this place is amazing. About a 25 minute walk not horrible, bed was comfortable room was clean. Not haunted at all despite the rumors. Overall a great experience."

Reviewed on Oct 5, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$167 nightly
The price is $199 total per night from Nov 1 to Nov 2
$199 total
Nov 1 - Nov 2
Total with taxes and fees
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 ...
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$143 nightly
The price is $170 total per night from Nov 1 to Nov 2
$170 total
Nov 1 - Nov 2
Total with taxes and fees
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 ...
8/10 Very Good! (2,417 reviews)
"The staff was just blatantly unhelpful. The front desk was often unmanned and could not take requests whether it was for a checkout or to ask about how a food delivery had been misplaced. I’ve seen HolidayInns with better customer service."

Reviewed on Oct 5, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 3,647 properties in Crestwood
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.
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
9/10 Wonderful! (1,353 reviews)
"Perfect location and great amenities. Texting with the property manager was a great way to get specific things we needed during our stay. The beds are super comfortable!"

Reviewed on Oct 4, 2026

Sentral Michigan Avenue
Kasa Lake Shore Chicago

Kasa Lake Shore Chicago

4 out of 5
446 East Ontario Street Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Popular attractions Michigan Avenue and Chicago Riverwalk are ...
Kasa Lake Shore Chicago
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
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 ...
9.4/10 Exceptional! (941 reviews)
"This would be great for both short or long-term stays. Excellent location: near CTA station, several food markets (Whole Foods, Trader Joe's, and Aldi in the same building), and great restaurants; both the river and the lake are within walking distance. As a highlight, the bedroom has a white-noise ..."

Reviewed on Oct 4, 2026

Kasa Magnificent Mile Chicago
See all properties in Crestwood
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.

Stay near popular Crestwood attractions

Hollywood Park

Have a fun-filled day with the family at Hollywood Park as part of your trip to Crestwood. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
LEGOLAND® Discovery Center Chicago

LEGOLAND® Discovery Center Chicago

$26
per adult
92% of travellers recommend
LEGOLAND® Discovery Center Chicago
Museum of Illusions Chicago Admission Ticket

Museum of Illusions Chicago Admission Ticket

$43
per adult
Museum of Illusions Chicago Admission Ticket
See all activities in Crestwood

Frequently asked questions

Is Crestwood worth visiting?
Crestwood is worth visiting for its diverse food scene, where travelers can enjoy Italian and Latin American cuisine, including dishes like pasta, tacos, and empanadas. The area also features standout attractions such as Hollywood Park, offering unique experiences for travelers.
When is the best time to visit Crestwood?
The best time to visit Crestwood is from May through September, when the climate is generally mild and pleasant. For fewer crowds and better value, consider traveling during the quieter months of December through March. These cooler winter months offer a different experience, with potential for snow in January and February.
What is a good itinerary length for Crestwood?
A good itinerary length for Crestwood is one to two days to explore Hollywood Park and enjoy local dining, with options including Italian, Latin American, and North American cuisine. An extended stay might allow for a more relaxed pace to savor these local flavors.
What are the top things to do in and around Crestwood?
In Crestwood, travelers can visit Hollywood Park, a notable local landmark and point of interest.
What cuisines can you find in Crestwood?
In Crestwood you can find Italian cuisine, with classic dishes like pasta, pizza, and lasagna. Travelers can also enjoy Mexican specialties such as tacos and enchiladas, along with North American comfort food, Chinese dishes, and fresh seafood options.
Can I book a refundable hotel in Crestwood?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Crestwood by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Crestwood with Expedia?
Expedia makes it easier to plan your Crestwood trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Crestwood?
The best choice depends on your travel style. Hotels in Crestwood can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Crestwood trip on Expedia?
Once you've booked your Crestwood trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Crestwood trip?
Expedia offers customer support before, during, and after your Crestwood trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Crestwood?
If it's your first trip to Crestwood, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Crestwood hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Crestwood hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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