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 Riu Plaza Chicago
Downtown Chicago
CA $1,281
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Honestly did not meet expectations. Check in was very fast but overall staff was a cold and not friendly. The only exception were few members at the breakfast restaurant, Maitre D’ and a few of the Bussers. No one offered help with the bags when checking in or out. We were traveling with a toddler and stroller so our hands were pretty full. Everyone seemed very interested in just chatting with other staff members and not connecting with guests at the hotel.
The rooftop seems to be adults only which was not mentioned after we asked reception about checking it out. We tried to go one day and they didn’t help get a high chair for our toddler. I even mentioned getting one from the second floor restaurant which they have and they said no. We ended up going somewhere else nearby instead. My son was not able to get a proper seat for his age. They pointed a a high top table which is absurd.
The hotel has great potential and well located. Unfortunately needs more presence in the hospitality aspect which should be their number one priority. Also note that they charge a $250 fee at checking-in addition to the nightly rate deposit. They claim is for incidentals but is just a way to encourage you spend the money at the hotel restaurant or bar.
Reviewed on Sep 9, 2026
Ready to book your vacation to Crestwood?
Crestwood Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $209
CA $248 total
Sep 10 - Sep 11
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $247
CA $293 total
Sep 10 - Sep 11
includes taxes & fees
8/10 Very good! (2,191 reviews)
"The most disappointing thing was not having access to any bottled water at all: none in the room, no vending machine, front desk had none, bar and restaurant were both closed at the time we really needed it, after being out in nearly 100 degree heat looking for the beach. The beach is near, meaning ..."
Reviewed on Sep 9, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (890 reviews)
"Great spot!"
Reviewed on Sep 7, 2026
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.
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.
What to do in Crestwood
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Frequently asked questions
How much does a Crestwood vacation package cost?
Offering excellent value package deals from CA $1,281 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?
- 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.
- 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.
- 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.
- 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.
