Crestwood Vacations from $558

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Your Crestwood Vacation

With plenty of highlights as well as hidden gems, this city is best explored with a Crestwood vacation package. Book a hotel in Hyde Park, which is good for history, nature and culture. A trip to Crestwood is a superb opportunity to do some sightseeing. Be sure to stop by well-known attractions like Chicago Ridge Shopping Mall, Trinity Christian College and Orland Square. Whatever your travel plans or budget, organizing your ultimate tailored Crestwood vacation is a piece of cake with Expedia.

The Latest Crestwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $558 per person
$558
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
The room was small, but fine. The bed was comfortable. The TV was too big so it covered the thermostat control panel, and the remote Guide button didn’t work. Also, the water pressure in the shower was super weak… glad I didn’t need to wash my hair. But location, general vibe, and staff were great.

Reviewed on Jul 8, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,130, price is now $721 per person
$721
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Hotel was clean and rooms were daily maintained. Also, Love how the hotel has a rooftop, and staff was always close by for anything you need. Definitely recommended 10/10

Reviewed on Jul 8, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $682 per person
$682
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
I loved the suite it was so spacious and they have a 24 hour fitness center! I enjoyed my stay there.

Reviewed on Jul 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,179, price is now $790 per person
$790
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Great place to stay for a night after exploring all day. I was able to see the city right from the window. Recommend this place for sure

Reviewed on Jul 8, 2026

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $863, price is now $579 per person
$579
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,939 reviews)
The property was outdated but fine. The room seemed clean. There was not rest during our stay here. You can hear everything going on outside and every door that opens and closes. There I security guard on the floor that keeps walking around and his radio is so loud, someone is constantly talking on the other side that we could not sleep multiple nights. It is in the great location but I would recommend paying little extra for some good sleep at night.

Reviewed on Jul 6, 2026

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Stay near popular Crestwood attractions

Hollywood Park

This family entertainment center offers go-karts, mini-golf, bumper cars, and a multi-floor arcade all in one vibrant location. Enjoy chef-crafted meals between activities for a complete day of fun.
See properties

What to do in Crestwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$22
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

$31
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in Crestwood

Crestwood Hotel Deals

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $308 total per night from Jul 26 to Jul 27
$308 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,877 reviews)
"I loved the suite it was so spacious and they have a 24 hour fitness center! I enjoyed my stay there."

Reviewed on Jul 8, 2026

Omni Chicago 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
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $183 total per night from Jul 9 to Jul 10
$183 total
Jul 9 - Jul 10
Total with taxes and fees
8.2/10 Very Good! (1,712 reviews)
"They had extra charges, when checking in to my room. Also, the couch had stains in my room and only one of us could take a shower. The shower was plugged and filled up with water. Would not drain."

Reviewed on Jul 8, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $239 total per night from Jul 9 to Jul 10
$239 total
Jul 9 - Jul 10
Total with taxes and fees
8/10 Very Good! (10,201 reviews)
"I had a one-night stay at the Congress Plaza Hotel with a friend. It is a historical building, so expect older facilities. The location is fabulous, and we can walk everywhere."

Reviewed on Jul 8, 2026

Congress Plaza Hotel
See all 3,551 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.

Find the Best Crestwood Vacation Packages

Crestwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
11,000
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Calumet Beach, Galloping Ghost and Midwest Carvers Museum

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Frequently asked questions

How much does a Crestwood vacation package cost?
Offering excellent value package deals from $558 on Expedia, you'll be thrilled with how little a vacation to Crestwood costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Crestwood?
You can generally find lower rates and greater availability in December, January and February. Browse our cheap Crestwood vacation packages and you could get some excellent off-season deals.
How many days is enough for Crestwood?
The ideal duration of your Crestwood vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to check out all the leading attractions and explore some hidden spots along the way.
How to find the best Crestwood package deals?
Use Expedia's handy filters to help you find some of the best Crestwood package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Crestwood package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Crestwood vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a personalized Crestwood vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Crestwood?
If you're considering a spur-of-the-moment Crestwood trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Crestwood?

  1. Pick your dates: What you'd like to do in Crestwood and your preferred season will help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Crestwood.
  3. Organize your Crestwood getaway with our trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Crestwood together.
  4. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Crestwood. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Crestwood vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some exciting things to do in Crestwood in Crestwood. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Crestwood vacation packages?
Set off on your dream escape to Crestwood with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until the next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up cheap deals before they sell out.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.