Crestwood Holidays from £1,378

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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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,139, price is now £1,378 per person
£1,378
per person
4 Sept - 11 Sept
found 19 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on 8 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,339, price is now £1,467 per person
£1,467
per person
12 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Clean, cozy, and updated. The shampoo and conditioner was amazing!! Consider selling it to guests!

Reviewed on 12 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,304, price is now £1,474 per person
£1,474
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was £2,144, price is now £1,404 per person
£1,404
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Loved the size of our room and how clean it was.

Reviewed on 9 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,541, price is now £1,680 per person
£1,680
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Parking Situation is kind of difficult, if you are staying at the Hotel parking should be included.

Reviewed on 12 Jul 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

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 £137 per night from 27 Jul to 28 Jul
£137
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,735 reviews)
"Great location, clean, and a super breakfast!"

Reviewed on 11 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
The price is £223 per night from 26 Jul to 27 Jul
£223
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,909 reviews)
"Great hotel with perfect and safe location. I loved the suite room with separate coach very roomy! The staff are the best, and the breakfast is great. Highly recommend this hotel!"

Reviewed on 12 Jul 2026

Omni Chicago Hotel
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 £168 per night from 10 Aug to 11 Aug
£168
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,233 reviews)
"Great value for the price"

Reviewed on 12 Jul 2026

Congress Plaza Hotel
See all 3,563 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

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

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

£24
per adult
96% of travellers recommend
Flyover in Chicago
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 £1,378. 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.

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. Flight-inclusive packages are ATOL protected.