Crestwood Vacations from $242

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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.
Holiday Inn Aurora North - Naperville by IHG

Holiday Inn Aurora North - Naperville by IHG

3 out of 5
Save 100% on your flight
Price was $368, price is now $242 per person
$242
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
7.8/10 Good! (784 reviews)
Room was clean . Unfortunately shower doors didn't Bathroom needs upgrades

Reviewed on Sep 8, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,749, price is now $1,028 per person
$1,028
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Beautiful hotel centrally located

Reviewed on Sep 16, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was $519, price is now $310 per person
$310
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
7.6/10 Good! (1,005 reviews)
Two mornings received poor service at breakfast. King bed in room. Could not open cabinet

Reviewed on Sep 15, 2025

Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Price was $491, price is now $309 per person
$309
per person
Dec 7 - Dec 13
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
8.2/10 Very Good! (1,011 reviews)
I always often stay here when visiting the area to see family. Thank you

Reviewed on Sep 16, 2025

OYO Hotel Portage I-94

OYO Hotel Portage I-94

2 out of 5
Price was $358, price is now $245 per person
$245
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
6.4/10 (730 reviews)
Very short stay. One night. Just needed a bed.

Reviewed on Sep 16, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Crestwood

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Crestwood

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% 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
96% 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
Fully refundableReserve now, pay when you stay
$176 nightly
The price is $207 total per night from Sep 22 to Sep 23
$207 total
Sep 22 - Sep 23
Total with taxes and fees
8.4/10 Very Good! (4,927 reviews)
First time exploring
"To start this hotel is extraordinary, the location is key if you want to explore Chicago. There is a Starbucks conveniently located outside and the grocery store across the street as well as multiple restaurants down the block. I would definitely rebook and consider this hotel as my first pick any ..."

Reviewed on Sep 15, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $197 total per night from Sep 22 to Sep 23
$197 total
Sep 22 - Sep 23
Total with taxes and fees
7.8/10 Good! (9,181 reviews)
"Beautiful older hotel in a great pedestrian area. Location to tours and sites was fantastic and we walked to everything we wanted to see and do. Only disappointing part is parking. There is a pay lot right next door but pricey and was only available in 24 hour time slots."

Reviewed on Sep 15, 2025

Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $215 total per night from Sep 22 to Sep 23
$215 total
Sep 22 - Sep 23
Total with taxes and fees
8.4/10 Very Good! (3,882 reviews)
"Bed is not comfortable. Pillows are not good. Staff are very friendly."

Reviewed on Sep 15, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 3,667 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.

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Frequently asked questions

How much does a Crestwood vacation package cost?
Offering excellent value package deals from $242 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

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.