Streeterville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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

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    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.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was CA $816, price is now CA $643 per person
CA $643
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Staff was great but next to fire station. Beware very noisy if staying city view

Reviewed on Feb 8, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,468, price is now CA $985 per person
CA $985
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Housekeeper left hair shedding in room but overall amazing hotel and great staff

Reviewed on Feb 12, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,409, price is now CA $1,720 per person
CA $1,720
per person
Apr 2 - Apr 6
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Price was CA $1,188, price is now CA $880 per person
CA $880
per person
Apr 9 - Apr 15
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
Everything was perfect and the front desk was so nice

Reviewed on Feb 10, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,157, price is now CA $884 per person
CA $884
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Where to stay in Streeterville

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

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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Mar 4 to Mar 5
CA $162
CA $228 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,323 reviews)
Friendly staff, tasteful room

Reviewed on Feb 11, 2026

Hotel Riu Plaza Chicago
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Feb 25 to Feb 26
CA $123
CA $144 total
Feb 25 - Feb 26
includes taxes & fees
8.6/10 Excellent! (3,066 reviews)
Everything was awesome at this hotel. From the attention and care of the desk staff to the fabulousness of the room and valet. Really great. Happy to stay there again.

Reviewed on Feb 10, 2026

Aloft Chicago Mag Mile
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Feb 24 to Feb 25
CA $122
CA $143 total
Feb 24 - Feb 25
includes taxes & fees
8.8/10 Excellent! (3,783 reviews)
Such great service, room was clean, and hotel staff were amazing! 10/10 recommend and will be staying here again when we come back!

Reviewed on Feb 4, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,687 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
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Frequently asked questions

How much does a Streeterville vacation package cost?
Maybe less than you might think — from as low as CA $643, 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.

Discover the most popular places to visit in Streeterville

John Hancock Center featuring a city, night scenes and landscape views

875 North Michigan Avenue

4.5/5(194 reviews)

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

875 North Michigan Avenue
Water Tower Place

Water Tower Place

4.5/5(67 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place
Chicago at New Year is the only way I know Chicago, I have no idea what it looks like without snow and ice!

Wrigley Building

4.5/5(8 reviews)

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the acclaimed theater scene and notable monuments in this vibrant area.

Wrigley Building

Things to do

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
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.