Crestwood Vacations from $319

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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 Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,094 reviews)
Shower door was off track. Had to struggle with it to gain entry to the shower. Overall, great experienc. Staff was excellent

Reviewed on Jul 13, 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,066 reviews)
Bathroom tile was loose and shower grout sisnr look to clean.

Reviewed on Jul 13, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
8.4/10 Very Good! (999 reviews)
Very disappointed with the lack of dining options and the fact that there’s no complimentary coffee or water available in the lobby. We will not stay here again

Reviewed on Jun 10, 2025

HYATT house Chicago/Schaumburg

HYATT house Chicago/Schaumburg

3.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 20
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (1,003 reviews)
Wasn’t as nice as I thought it would be. Very plain. Needs a lot of updating. It is clean though.

Reviewed on Jun 6, 2025

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,000 reviews)
Clean, great location .

Reviewed on Jul 12, 2025

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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

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

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $210 total per night from Jul 27 to Jul 28
$210 total
Jul 27 - Jul 28
Total includes taxes and fees
7.8/10 Good! (8,941 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
$231 nightly
The price is $266 total per night from Aug 10 to Aug 11
$266 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (2,029 reviews)
"Clean, great location ."

Reviewed on Jul 12, 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
$151 nightly
The price is $178 total per night from Aug 10 to Aug 11
$178 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 3,548 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 $319 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.