Book Exclusive Crestwood Vacation Packages

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Crestwood flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 14 - Aug. 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Willis Tower and Chicago Riverwalk are located nearby.

Top Crestwood hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $226 per night
CA $226
per night
May 27 - May 28
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
Breakfast available
Parking available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $194 per night
CA $194
per night
May 27 - May 28
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Parking available
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $171 per night
CA $171
per night
May 27 - May 28
Book a stay at this family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $246 per night
CA $246
per night
May 29 - May 30
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Spa
Parking available
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is CA $205 per night
CA $205
per night
May 27 - May 28
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Pool
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $168 per night
CA $168
per night
May 27 - May 28
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Parking available
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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

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place

Crestwood Vacations

You don't have to know everything about the place to have an incredible time in Crestwood, but you will need to have an idea about a few basic facts before you jet off.

About 17 miles (27 kilometers) to the south of central Chicago, Crestwood is just one of the neighborhoods that make this city so fabulous.

Forget the big-name attractions — it's the locals that make a place tick. Here in Chicago, there are 2,700,000 of them.

Places to visit in Crestwood

The Chicago region offers lots of opportunities to have fun outdoors. Why not make plans to go mountain biking while you're here? If you'd love to turn up the fun factor, also get out and go rock climbing.

Where do you fly into for Crestwood?

All ready to kick-start your next thrilling escape? Well, Crestwood is about 10 miles (16 kilometers) from Midway International Airport (MDW).

Frequently asked questions

How much are vacation packages to Crestwood?
Starting from as low as CA $1,145, flight and hotel packages are an excellent way to stretch your travel budget. Crestwood, here you come!
Where can I get the best vacation package deals for Crestwood?
Walking away with the best package deal to Crestwood is a cinch with Travelocity. With around 400 airlines and 665,000 properties worldwide, the choice is yours when it comes to selecting your hotels and flights.
Why should I book my Crestwood vacation bundle via Travelocity?
With exceptional service, customer support available 24/7 and some of the most idyllic escapes on offer, you’ll never roam alone. And if you happen to find a lower price, we’ll match it. That’s our Price Match Guarantee.
Will I save money on my Crestwood car rental if I book it with hotels and flights?
Booking a Crestwood vacation package with Travelocity is an easy way to save your hard-earned money. Pick a flight, car and hotel, or any combination of them, and score awesome discounts. It’s also possible to throw in experiences. After you’ve collected the keys to your rental car, venture out of the neighborhood and discover what this location has to offer. Roughly 85 kilometersfrom Crestwood, Six Flags Great America is certainly worth a road trip.
What is the best time of year to go to Crestwood?
If you’re eager to avoid expensive flights, big crowds and booked-out hotels, organize your escape outside of . The quietest time to visit Crestwood is . You’ll find hotel rates are the highest in and the most economical in .
Where should I stay when visiting Crestwood?
When looking for a place to base yourself in Crestwood, the Holiday Inn Express Crestwood is a good place to start. Many travelers choose to lay their heads at this top option.
Can I go on vacation to Crestwood at this time?
Don’t head to Crestwood without the facts about travel restrictions and quarantine policies. Travelocity’s Covid-19 Travel Advisor will fill in the blanks. Our travel experts have pulled together all the info you need to make your vacation and flight as stress-free as possible.