Crestwood Holidays

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Top hotels in Crestwood

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 Rp2.944.136 per night from 27 Jul to 28 Jul
Rp2.944.136
Rp3.500.450 total
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,690 reviews)
"We like our room, very clean and spacious"

Reviewed on 4 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 Rp2.181.427 per night from 7 Jul to 8 Jul
Rp2.181.427
Rp2.593.501 total
7 Jul - 8 Jul
includes taxes & fees
8/10 Very good! (10,170 reviews)
"First, the parking is not accessible through the building. It was raining when we arrived. The parking is a regular open lot that is $62 and nothing special. You cannot enter the building from the parking lot. We had to walk over a block in the rain carrying all our luggage. Next, when we stepped ..."

Reviewed on 5 Jul 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp2.629.927 per night from 8 Jul to 9 Jul
Rp2.629.927
Rp3.724.708 total
8 Jul - 9 Jul
includes taxes & fees
9.2/10 Wonderful! (1,849 reviews)
"Hotel has a great location. Front door staff is outstanding with a strong service ethos. Rooms are large and functional. Only complaint is the elevators were not all working; as a result there could be long waits. Restaurant and bar staff were super attentive and knowledgeable."

Reviewed on 5 Jul 2026

Omni Chicago Hotel
See all 3,555 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.

Stay near popular Crestwood attractions

Hollywood Park

This family entertainment centre offers go-karts, mini-golf, bumper cars, and a multi-floor arcade all in one vibrant location. Enjoy chef-crafted meals between activities for a complete day of fun.
See properties

What to do in Crestwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp433.974
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

Rp438.617
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.946.631
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Crestwood

Frequently asked questions

How much does a Crestwood holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday package, consider travelling 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Crestwood holiday as a package?
Expedia holiday 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 personalised Crestwood holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 holiday 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 accommodation 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 customised Crestwood holiday package.

Explore a world of travel with Expedia

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