Streeterville Vacation Packages
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Top Holiday Package Deals in Streeterville
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was CA $1,047, price is now CA $766 per person
CA $766
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (3,921 reviews)
The staff were super friendly, parking lot across the street and the location is wonderful. I would definitely stay again with my grandchildren. We took in all the Chicago sites.
Reviewed on Jun 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,854, price is now CA $1,316 per person
CA $1,316
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
This is our second time staying at the sable and it was wonderful! The staff is amazing and friendly! The elevators were out and we got lost a couple times getting to our room, and every single staff member that we would run into each time was so helpful and kind in finding where we were supposed to go! One of the housekeepers even stopped what she was doing to walk us to our correct floor when she realized we were lost! She was so incredibly nice! The views are incredible, the location is incredible, and the staff is incredible! Will definitely be coming back on our next trip to Chicago/Navy Pier!
Reviewed on Jun 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,941, price is now CA $1,396 per person
CA $1,396
per person
Sep 4 - Sep 7
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.
Reviewed on Jun 12, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,417, price is now CA $1,029 per person
CA $1,029
per person
Aug 13 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,083, price is now CA $797 per person
CA $797
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,791 reviews)
Old hotel and rooms. All the outlets in our room were titled and so hard to plug things in them. The outlets near the nightstands on either sides can’t accommodate a charger because they’re stuck on the side of the nightstand between it and the side of the bed. Hairdryer so old and didn’t work. Check in was exactly at 4, they weren’t lenient when I showed up at 2:40.
Reviewed on Jun 10, 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
5 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.
Streeterville Hotel Deals
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $201 per night from Jun 14 to Jun 15
CA $201
CA $239 total
Jun 14 - Jun 15
includes taxes & fees
7.8/10 Good! (1,568 reviews)
"I"
Reviewed on Jun 12, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jul 8 to Jul 9
CA $223
CA $305 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (4,424 reviews)
"This is a new hotel (2024) but you can already see wear and tear. It’s maybe slightly better than a holiday inn. The blanket is a little weird in that’s it’s a fleece between two sheets. It’s clear the fleece isn’t washed between stays as you can see hair. I agree with other reviews that not having ..."
Reviewed on Jun 12, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jun 30 to Jul 1
CA $223
CA $265 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (4,412 reviews)
"Extremely quiet, comfortable and nice."
Reviewed on Jun 11, 2026
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
Discover the most popular places to visit in Streeterville
Water Tower Place
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
875 North Michigan Avenue
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.
900 North Michigan Shops
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 theater scene in this vibrant area.
Things to do
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
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.