Streeterville Vacation Packages
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Top Holiday Package Deals in Streeterville
Price found within the past 48 hours. Click for updated prices.
Hotel 505 River North
Downtown Chicago
CA $1,216
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,924 reviews)
Overall really great location & good experience. They did miss cleaning my room the second day (which I would have appreciated) but not the end of the world. Would stay again!
Reviewed on Oct 12, 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
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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Streeterville Hotel Deals
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
CA $183
CA $218 total
Nov 11 - Nov 12
includes taxes & fees
8/10 Very good! (2,382 reviews)
"We booked a 2-double queen-bed room but were given a king suite & 2 cots for 4 people. The whole building was really hot even though the thermostat in our room was set to 68. Staff was friendly. Just shouldn’t overbook if that’s the case."
Reviewed on Oct 13, 2026
The Wade
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
CA $181
CA $215 total
Nov 12 - Nov 13
includes taxes & fees
8.6/10 Excellent! (2,150 reviews)
"Great location for those that want to be downtown with easy access to everything!"
Reviewed on Oct 13, 2026
Hotel Saint Clair- Magnificent Mile
162 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
CA $189
CA $228 total
Nov 12 - Nov 13
includes taxes & fees
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.
Frequently asked questions
How much does a Streeterville vacation package cost?
Maybe less than you might think — from as low as CA $1,216, 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
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.
875 North Michigan Avenue
9.2/10 (2,926 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 fascinating museums.
Tribune Tower
8.6/10 (76 reviews)
You can learn about the history of Chicago with a stop at Tribune Tower. Discover the fascinating museums and notable monuments in this vibrant area.
Photo by Rita Irvine
900 North Michigan Shops
8.6/10 (55 reviews)
You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Photo by daniel jersey
Chicago Children's Museum
9.2/10 (237 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.
360 CHICAGO
You can learn about the history of Chicago with a visit to 360 CHICAGO. Amble around this vibrant area's riverfront or experience its entertainment choices.
Museum of Contemporary Art Chicago
9.0/10 (88 reviews)
You can spend an afternoon browsing the exhibits at Museum of Contemporary Art Chicago during your travels in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Broadway Playhouse
8.4/10 (17 reviews)
You can enjoy a show at Broadway Playhouse during your stay in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Things to do
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.