Crestwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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.

Top Crestwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.4/10 Very Good! (1,950 reviews)
The property was very nice until we got to the room. The room seemed more dark and dingy. Very expensive for the quality of the room. Staff were extremely nice and the hotel was more central to different parks and modes of transportation.

Reviewed on Jul. 2, 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.4/10 Very Good! (1,755 reviews)
beautiful hotel, friendly and helpful staff.

Reviewed on Jul. 2, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.

Reviewed on Jun. 27, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 5 - Sep 8
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
per person
Sep 3 - Sep 7
just found
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
No reviews

Ready to book your vacation to Crestwood?

 

Choose your dates

Crestwood Hotel Deals

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
The price is CA $208 per night from Jul 10 to Jul 11
CA $208
CA $244 total
Jul 10 - Jul 11
includes taxes & fees
8.8/10 Excellent! (2,362 reviews)
"Staff were really nice and accommodating. I was able to check in early and check out late for free. The room was decent. Outdated but it was clean. Would book again."

Reviewed on Jul. 2, 2025

Hilton Chicago/Magnificent Mile Suites
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is CA $310 per night from Jul 6 to Jul 7
CA $310
CA $407 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,967 reviews)
"It was our first time in staying in Chicago and we couldnt have picked a better resort!!"

Reviewed on Jul. 3, 2025

InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Jul 7 to Jul 8
CA $162
CA $190 total
Jul 7 - Jul 8
includes taxes & fees
7.8/10 Good! (8,944 reviews)
"Hospitality was amazing and room was beautiful."

Reviewed on Jul. 2, 2025

Congress Plaza Hotel
See all 3,538 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Crestwood

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

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

Michigan Avenue

4.5/5(19 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

CA $67
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

CA $62
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

CA $61
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Crestwood

Frequently asked questions

How much does a Crestwood vacation package cost?
Offering excellent value package deals from CA $748 on Expedia, you'll be thrilled with how little a vacation to Crestwood costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Crestwood?
January, February and April are great times to search for cheap Crestwood vacation packages. Choosing to travel in quieter periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Crestwood?
Dedicate at least 2 days for your Crestwood vacation to really immerse yourself in all that makes this destination unique. Stroll around popular areas, including Ashburn and Hazel Green. Then head to the major sights like Hollywood Park and Childrens Museum of Oak Lawn. With a well-organized itinerary, you'll be kept busy with room for some me-time too. Want to travel outside of Crestwood? Consider fitting in an excursion or two.
How to find the best Crestwood package deals?
Begin your search for a Crestwood package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Crestwood package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Crestwood getaway off to a flying start.
Is it cheaper to book a Crestwood vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Crestwood escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Crestwood?
If you have your Crestwood travel dates confirmed, book early to grab some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Crestwood?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Crestwood.
  2. Set a budget: Consider expenses such as flights, meals and transportation when calculating how much to save for your trip to Crestwood. Then, choose a hotel that works with your budget, whether that's an affordable stay or a more luxurious getaway.
  3. Decide how long to go for: Now that you know more about Crestwood, you can figure out the right length of your vacation. Pull together a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Crestwood vacation package for you.

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