Crestwood Trips (flight + hotel)

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Top hotels in Crestwood

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
The price is P8,056 per night from 20 Apr to 21 Apr
P8,056
P9,457 total
includes taxes & fees
Apr 20 - Apr 21
8.2/10 Very Good! (3,852 reviews)
"Had to take uber to all sights we wanted to visit. Certain foods would run out if you weren’t there early."

Reviewed on Apr 6, 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P8,961 per night from 16 Apr to 17 Apr
P8,961
P12,205 total
includes taxes & fees
Apr 16 - Apr 17
8.8/10 Excellent! (2,039 reviews)
"Convenient location"

Reviewed on Apr 7, 2025

Swissotel - Chicago
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is P5,284 per night from 20 Apr to 21 Apr
P5,284
P6,203 total
includes taxes & fees
Apr 20 - Apr 21
8.6/10 Excellent! (1,018 reviews)
"The property is awesome! The only issue is I have severe allergies and I can tell that there was an animal in the room prior to me."

Reviewed on Apr 4, 2025

Crowne Plaza Chicago West Loop by IHG
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.

Frequently asked questions

How much does a Crestwood vacation package cost?
Offering excellent value package deals 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?
If you’d like to book a cheap Crestwood vacation package, consider traveling in January, February and April. You’re likely to find better rates on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Crestwood?
The ideal length of your Crestwood vacation depends on what you’d like to do. Generally, a few days to a week will give you plenty of time to tick off all the major sights and explore some hidden treasures 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. Choose when to get away: Check your diary and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Crestwood.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodations will probably be the largest expense during your trip to Crestwood.
  3. Decide how many days away: Start by compiling a list of the attractions you want to experience in Crestwood. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Crestwood vacation package.

Popular places to visit

What to do in Crestwood

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