Crestwood Vacation Packages

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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.

Top Crestwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,158, price is now CA $875 per person
CA $875
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,079 reviews)
The hotel was a good area, walking distance of everything. Have zero complaints.

Reviewed on Aug 6, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,513, price is now CA $1,004 per person
CA $1,004
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,908, price is now CA $1,359 per person
CA $1,359
per person
Sep 14 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,832 reviews)
Great breakfast

Reviewed on Aug 6, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,449, price is now CA $1,782 per person
CA $1,782
per person
Oct 17 - Oct 20
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
Price was CA $1,380, price is now CA $1,040 per person
CA $1,040
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.4/10 Very good! (2,238 reviews)

Ready to book your vacation to Crestwood?

 

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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
The price is CA $201 per night from Aug 30 to Aug 31
CA $201
CA $239 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (10,214 reviews)
"Know that this is a very old hotel that hasn't seen a material renovation in decades. AC system is ancient, TVs are tiny. No overhead lighting. Blue tile bathroom with rusty fixtures. But the rooms are big and ours had walk in closets. And great location."

Reviewed on Aug 6, 2026

Congress Plaza 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
The price is CA $206 per night from Aug 30 to Aug 31
CA $206
CA $245 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,930 reviews)
"Always love staying at the ambassador! So much old charm but modern amenities and gorgeous design. Located in a lovely quiet neighborhood north of the loop with lots of walkable cafes and restaurants."

Reviewed on Aug 6, 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Aug 30 to Aug 31
CA $246
CA $337 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (2,729 reviews)
"The property was old and defiantly not 4 star hotel. At best its a 3 Star hotel. Location was great"

Reviewed on Aug 5, 2026

The Allegro Royal Sonesta Hotel Chicago Loop
See all 3,625 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
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Stay near popular Crestwood attractions

Hollywood Park

Have a fun-filled day with the family at Hollywood Park as part of your trip to Crestwood. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
See properties

What to do in Crestwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $70
per adult
92% of travellers recommend
Chicago By Night River and 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 $875 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.