Crestwood Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Crestwood

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is S$215 per night from 4 Aug to 5 Aug
S$215
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,919 reviews)
"It’s a historical building so it does have its worn down look. Beautiful overall. I just wish it wasn’t so expensive"

Reviewed on 8 Jul, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is S$376 per night from 24 Jul to 25 Jul
S$376
24 Jul - 25 Jul
includes taxes & fees
9/10 Wonderful! (2,000 reviews)
"Central to everything, very safe, and walking distance or a short drive to a lot of things. The hotel staff was also very accommodating. We would definitely stay here on our next stay!"

Reviewed on 8 Jul, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is S$264 per night from 10 Jul to 11 Jul
S$264
10 Jul - 11 Jul
includes taxes & fees
8.8/10 Excellent! (2,397 reviews)
"Staff was amazing, and rooms were clean and comfortable! Overall a great stay"

Reviewed on 6 Jul, 2025

Hilton Chicago/Magnificent Mile Suites
See all 3,548 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Crestwood

River tour boat in Chicago

Architecture River Tour

S$62
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

S$58
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

S$58
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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.