Crestwood Vacations from $339

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,010 reviews)
Property was being remodeled. Room was dirty, noisey and dated. Tub/shower unsafe for older guests

Reviewed on Jun 19, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,039 reviews)
Outstanding breakfast!

Reviewed on Jun 23, 2025

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Save 100% on your flight
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
9/10 Wonderful! (19 reviews)
Very up to date modern property.

Reviewed on Jun 24, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on Jun 24, 2025

The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Good accommodation. Quiet, clean and spacious. Close to almost anything in downtown Chicago. Only qualm is the somewhat odd entry thru an office building which requires a badge, take the elevator to the 39th floor, and then another elevator to the 40th floor. But it's worth the effort.

Reviewed on Jun 21, 2025

Don't see what you're looking for?
See all available trips from Columbus to Crestwood
View all trips

Discover the most popular places to visit in Crestwood

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Crestwood

River tour boat in Chicago

Architecture River Tour

$49
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Crestwood

Crestwood Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
$162 nightly
The price is $190 total per night from Jul 7 to Jul 8
$190 total
Jul 7 - Jul 8
Total includes taxes and fees
8.4/10 Very Good! (4,261 reviews)
"Yes"

Reviewed on Jun 24, 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
$189 nightly
The price is $216 total per night from Jul 1 to Jul 2
$216 total
Jul 1 - Jul 2
Total includes taxes and fees
9/10 Wonderful! (1,919 reviews)
"Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual."

Reviewed on Jun 24, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Jul 6 to Jul 7
$159 total
Jul 6 - Jul 7
Total includes taxes and fees
8.8/10 Excellent! (2,328 reviews)
"I loved the view from my room. Everything was great except the parking situation. 80 to 90$ a day to park so add that into your stay if you’re on a budget like me. Nice big tv’s."

Reviewed on Jun 22, 2025

Hilton Chicago/Magnificent Mile Suites
See all 3,527 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

More vacations you might like

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Crestwood vacation package cost?
Offering excellent value package deals from $339 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.