Streeterville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Streeterville

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $2,730, price is now CA $1,207 per person
CA $1,207
per person
Dec 19 - Dec 23
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,734, price is now CA $2,634 per person
CA $2,634
per person
Dec 27 - Jan 2
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,785, price is now CA $2,704 per person
CA $2,704
per person
Dec 27 - Jan 2
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $1,950, price is now CA $1,402 per person
CA $1,402
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Always the best hotel in Chicago!!!!

Reviewed on Nov 2, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,000, price is now CA $1,481 per person
CA $1,481
per person
Dec 27 - Jan 2
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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

Streeterville Hotel Deals

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 $166 per night from Nov 24 to Nov 25
CA $166
CA $198 total
Nov 24 - Nov 25
includes taxes & fees
8.6/10 Excellent! (2,191 reviews)
"Very nice and comfortable"

Reviewed on Nov 3, 2026

The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Nov 9 to Nov 10
CA $146
CA $174 total
Nov 9 - Nov 10
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
162 East Ontario Street Chicago IL
The price is CA $142 per night from Nov 22 to Nov 23
CA $142
CA $172 total
Nov 22 - Nov 23
includes taxes & fees
Hotel Saint Clair- Magnificent Mile
See all 4,609 properties in Streeterville
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 Streeterville vacation package cost?
Maybe less than you might think — from as low as CA $1,207, in fact! By bundling hotels, flights and car rentals into a custom-built vacation package, your Streeterville escape is just clicks away.
How do I get a cheap travel package to Streeterville?
Combine your flight and hotel bookings, throw in extras such as a rental car or activities, and save with a Streeterville vacation package. You won't just pick up amazing discounts on your adventure — you'll have loads of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 hotels throughout the world. Your dream vacation starts right here, right now!
Where should I stay in Streeterville?
Most people who travel to Streeterville include both McCormick Place and Millennium Park on their must-see lists. Why not reserve a hotel near these main attractions?
What are the top hotels in Streeterville?
Make a reservation at Sable at Navy Pier Chicago, Curio Collection by Hilton. It's one of the neighborhood's most in-demand hotels. Another well-known option in Streeterville is Omni Chicago Hotel.
How far in advance should I book my Streeterville 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 stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Streeterville travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to crafting your Streeterville getaway, you're in charge!
What should I know before booking a Streeterville travel package?
Booking all the parts of your getaway together is one of the easiest ways to save. Bundle your car rentals, airfares and hotels into a neat package. But you're not restricted to hotels. Expedia offers all sorts of properties, including vacation rentals such as mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Streeterville Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just select the carrier you want and create your ideal Streeterville vacation.
If I'm not able to travel, can I cancel my Streeterville vacation package?
Yes you can, and we're here to help. You may be able to cancel or amend your Streeterville vacation package for free if you booked in the last 24 hours. However, you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, browse our Customer Service Portal for more information.

Stay near popular Streeterville attractions

A city intersection with tall buildings, including a historic building labeled "Water Tower Place."

Water Tower Place

9.0/10 (1,113 reviews)
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.