Smith Park Vacation Packages

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Top Holiday Package Deals in Smith Park

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $770, price is now CA $485 per person
CA $485
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
loved our stay, great hotel and friendly staff

Reviewed on Sep. 3, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,853, price is now CA $1,693 per person
CA $1,693
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug. 31, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,667, price is now CA $1,008 per person
CA $1,008
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Best, very clean, best view, really enjoyed the stay!

Reviewed on Sep. 2, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,043, price is now CA $655 per person
CA $655
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
This hotel was lovely. The room was large and smelled divine. Everything was spotless, beds were comfy, location was excellent, staff were friendly and accommodating. Would definitely stay here again. :)

Reviewed on Sep. 4, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $856, price is now CA $545 per person
CA $545
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,007 reviews)
Great location, great service

Reviewed on Sep. 4, 2025

Where to stay in Smith Park

Find the best Smith Park areas and neighborhoods for the activities you enjoy most. Learn more about Smith Park
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Smith Park Hotel Deals

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 CA $204 per night from Sep 22 to Sep 23
CA $204
CA $239 total
Sep 22 - Sep 23
includes taxes & fees
Congress Plaza Hotel
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
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Sep 22 to Sep 23
CA $253
CA $297 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Sep 22 to Sep 23
CA $230
CA $270 total
Sep 22 - Sep 23
includes taxes & fees
The Wade
See all 4,810 properties in Smith Park
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Smith Park vacation package cost?
Our Smith Park vacation packages, which start at just CA $485, are the best way to save big bucks. Choose your preferred hotels, flights and more to create a personalized trip.
How do I get a cheap travel package to Smith Park?
You'll save a pile of money if you combine your hotels, car rentals and flights into a Smith Park travel package. Sometimes cheap means fewer choices. But that's not the case with Expedia. We offer more than 550 air carriers and 1,000,000 properties globally, which means you'll always have plenty of variety to choose from. Want to save even more? Add some fun activities to your package deal and unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Smith Park?
Most travelers who visit Smith Park include University of Illinois Chicago and United Center on their itineraries. Why not book a hotel as close as possible to these iconic attractions?
How far in advance should I book my Smith Park vacation?
Travelers are usually able to browse international flights on Expedia up to 12 months prior to departure. Booking at the last minute? With a little bit of luck, it's still possible to nab a cheaper ticket just weeks before your flight.
What does an Expedia Smith Park travel package include?
Packages include rental cars, hotels and flights, but you can combine any of them to create your ideal Smith Park escape. You can also add on some tours and activities once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Smith Park travel package?
Whether it's adventure or relaxation you're seeking, a Smith Park vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Smith Park Expedia vacation package?
You can, and with over 550 airlines to pick from globally, you've got lots of choice. Search the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Smith Park vacation package?
If your travel plans in Smith Park have been upended, it's comforting to know that it's possible to cancel or amend your booking. If you booked less than 24 hours ago, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Smith Park

Wrigley Field featuring central business district, a city and a sporting event

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 signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy 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

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
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

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.