Crestwood Holidays from £648

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Your Crestwood Holiday

With plenty of highlights as well as hidden gems, this city is best explored with a Crestwood holiday 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, organising your ultimate tailored Crestwood holiday is a piece of cake with Expedia.

Top Crestwood Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
per person
12 Sept - 16 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
All staff were very friendly and helpful. Hotel was in convenient location for walking.

Reviewed on 27 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 20 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Great, comfortable beds, spacious rooms. The bathroom was very clean and spaciousZ loved it

Reviewed on 3 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
8 Sept - 12 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on 1 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 20 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 20 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,031 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on 30 Jul 2025

Crestwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
11,000
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Galloping Ghost, Calumet Beach and Midwest Carvers Museum

Top hotels in Crestwood

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 £119 per night from 1 Sept to 2 Sept
£119
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,938 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on 1 Aug 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
The price is £204 per night from 1 Sept to 2 Sept
£204
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (2,160 reviews)
"Great view"

Reviewed on 2 Aug 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
Fully refundableReserve now, pay when you stay
The price is £127 per night from 17 Aug to 18 Aug
£127
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,562 reviews)
"Nice clean hotel, good location."

Reviewed on 2 Aug 2025

Hilton Chicago/Magnificent Mile Suites
See all 3,676 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Crestwood

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

£22
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

£33
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Crestwood

Frequently asked questions

How much does a Crestwood travel package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Crestwood from just £648. And the more you bundle, the more cash you save. Your dream holiday has never been more affordable.
If I'm not able to travel, can I cancel my Crestwood travel package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Crestwood travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to learn more.
How do I get a cheap travel package to Crestwood?
Bundling your flight and hotel with Expedia won't just save precious time — it'll save you cash too. A Crestwood travel package makes it a cinch to put together your ideal trip. With more than 550 airlines worldwide to pick from, finding convenient flights that fit your schedule won't be a hassle. On top of that, we've got over 1,000,000 hotel options globally to take your pick of. Now that's choice! No matter who you are, Expedia puts more of the world within your reach.
Does Expedia offer Book Now, Pay Later Crestwood holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a terrific getaway without hurting your hip pocket. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna can help. Paying in easy monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: Like the idea of paying for your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: Clicking the "book now" button is much easier with this payment option. Just put down a small deposit on your booking and then start working on your travel itinerary.

Where should I stay in Crestwood?
With interesting attractions like Gaelic Park and Trinity Christian College in this neighbourhood, try to find a hotel near either one. Lake Katherine Nature Centre is another sight in Crestwood that draws the crowds.
What are the top hotels in Crestwood?
Get your escape off to a good start by booking a room at Hyatt Regency Chicago. It's one of most popular hotels in Crestwood. Another cosy option is The Godfrey Hotel Chicago.
How far in advance should I book my Crestwood holiday?
Smart travellers will likely want to reserve their seats as early as possible. You can normally look up international fares on Expedia up to 12 months before your intended flight. If you're purchasing your ticket at the last minute, don't worry. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Crestwood travel package include?
Hotels, rental cars and flights, or any combination of them — the choice is all yours! Whether you're exploring Crestwood with the family or travelling solo, there's a bundle to fit your style and budget. Once you've made your booking, why not add on one or two activities?
What should I know before booking a Crestwood travel package?
Whether it's relaxation or adventure you're seeking, a Crestwood travel package lets you plan your escape your way. Plus, you'll score great discounts just for combining your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Crestwood Expedia travel package?
Yes — that's one of the best things about an Expedia package. You can pick and choose your flights, hotels and more. We have more than 550 airline partners across the globe, so you have options galore when organising your Crestwood getaway.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.