Streeterville Vacation Packages

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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
per person
Jul. 2 - Jul. 6
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
This was a really nice hotel in a great area with tons of restaurants, well lit up streets and easy walking in the downtown River North area. The hotel itself was lively on the ground floor with its bar and restaurant and the room was clean and well laid out and quiet overall The bed/pillows were really, really comfortable. I would stay here again anytime.

Reviewed on May 18, 2024

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)
7.8/10 Good! (1,743 reviews)
Just overall a really nice place

Reviewed on May 22, 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 2 - Jul. 6
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
EXCEPTIONAL SERVICE!!

Reviewed on May 21, 2024

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)
8.2/10 Very Good! (1,509 reviews)
Balcony views were great! Staff was friendly and the room was a decent size. The only thing I would say needs improvement would be the cleanliness of the rooms and bathroom.

Reviewed on May 23, 2024

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)
8.8/10 Excellent! (1,018 reviews)
Everything was awesome.

Reviewed on May 19, 2024

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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Streeterville Hotel Deals

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 $180 per night from May 28 to May 29
CA $180
CA $211 total
includes taxes & fees
May 28 - May 29
8.4/10 Very Good! (2,218 reviews)
Not bad
"Great stay for spring break. Value was great and location was excellent."

Reviewed on May 21, 2024

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 $241 per night from May 27 to May 28
CA $241
CA $283 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (1,465 reviews)
"Really enjoyed our stay here! Valet parking is definitely the way to do it if you’re driving into the cities. It was a little hectic but once we got all settled in it was an easy check in from there! Would definitely stay here again!"

Reviewed on May 24, 2024

Hilton Chicago/Magnificent Mile Suites
W Chicago - Lakeshore
W Chicago - Lakeshore
4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Jun. 17 to Jun. 18
CA $261
CA $307 total
includes taxes & fees
Jun 17 - Jun 18
8/10 Very Good! (1,001 reviews)
"located right on Laker Michigan, the view was amazing. Only a block walk to get to the lakeshore walking path, and less than a 1 mile to Navy pier, the Art Institute of Chicago. Lots of great restaurants nearby."

Reviewed on May 21, 2024

W Chicago - Lakeshore
See all 4,051 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.

Explore other types of vacation packages

All Inclusive Vacations

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 $674, 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

Image for 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
Image for John Hancock Center

John Hancock Center

4.5/5(194 reviews)

You can find out about the history of Chicago with a visit to John Hancock Center. Amble around this vibrant area's lakeside or experience its fascinating museums.

John Hancock Center
Image for Chicago Children's Museum

Chicago Children's Museum

4.5/5(14 reviews)

You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Chicago Children's Museum

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $311
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

CA $138
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
Image for Chicago Evening Crime Tour by Bus

Chicago Evening Crime Tour by Bus

CA $70
Per adult
100% of travellers recommend
Chicago Evening Crime Tour by Bus
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.