Streeterville Vacation Packages

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Top Holiday Package Deals in Streeterville

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jun. 30 - Jul. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago

Reviewed on May 10, 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 16 - Jul. 20
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,009 reviews)
I loved it plan on staying again

Reviewed on May 10, 2024

Hotel Arista

Hotel Arista

4.5 out of 5
per person
Jul. 4 - Jul. 8
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
The stay was good , staff, good, room good. Hidden ammenity charge of 7.95 a night to have access to amenities. Not the use of them, thats extra. Just the availability of the ammenity. Its not the amount. Its adding it on at the end. Im tired of hidden fees and BS charges. If you want more for the room tell me up front. I will not stay here again out of principle.

Reviewed on May 6, 2024

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
Jun. 30 - Jul. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Is a beautiful, clean and nice Hotel. Large and extremely comfortable rooms. I do not recommend having a car because parking is extremely expensive.

Reviewed on May 10, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Jul. 5 - Jul. 8
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.6/10 Exceptional! (970 reviews)
Everything exceeded our expectations and would highly recommend! Stunning rooms that make the Ritz and Four Seasons look pathetic!

Reviewed on May 2, 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
The price is CA $216 per night from May 27 to May 28
CA $216
CA $254 total
includes taxes & fees
May 27 - May 28
8.4/10 Very Good! (2,192 reviews)
"Great service, affordable, safe, lots of things nearby. You can walk everywhere."

Reviewed on May 7, 2024

Aloft Chicago Mag Mile
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
105 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from May 12 to May 13
CA $163
CA $192 total
includes taxes & fees
May 12 - May 13
8/10 Very Good! (3,420 reviews)
"Bathroom tub handle broken, difficult to turn on. Dirty bathroom floor. Staff responsiveness, professionalism and helpfulness excellent. Felicia very helpful."

Reviewed on May 9, 2024

The Whitehall Hotel, BW Premier Collection
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 $208 per night from May 27 to May 28
CA $208
CA $244 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (1,452 reviews)
"Customer service"

Reviewed on May 8, 2024

Hilton Chicago/Magnificent Mile Suites
See all 4,112 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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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 $826, 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 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 acclaimed art scene.

John Hancock Center
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 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 fascinating museums.

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 Museum of Contemporary Art: General Admission Ticket

Chicago Museum of Contemporary Art: General Admission Ticket

CA $30
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

CA $138
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
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.