Crestwood Holidays from £1,017
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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.
Trump International Hotel & Tower Chicago
Downtown Chicago
£1,588
per person
3 Nov - 10 Nov
found 13 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Nice place and location, especially if you have a good room. It's expensive but you get good experiance
Reviewed on 26 Aug 2026
Swissotel - Chicago
Downtown Chicago
£1,152
per person
3 Nov - 10 Nov
found 13 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
The views are nice. The room is more simple. The bathroom needs to be upgraded. Definitely just 3.5-4*. The late night snack area is a nice feature though.
Reviewed on 25 Aug 2026
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
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£89
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£117
30 Aug - 31 Aug
includes taxes & fees
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.
What to do in Crestwood
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
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 £1,017. 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.
