Streeterville Vacations from $236
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Your Streeterville Vacation
Experience the best that Streeterville has to offer with a Streeterville vacation package. From its families and history to its culture and more, you'll quickly be won over by this lakeside neighborhood. Wondering what to see and do during your trip to Streeterville? Nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago are excellent places to start. Don't just wish for it — turn it into reality! Lock in your perfect Streeterville vacation with Expedia and experience travel your way.
The Latest Streeterville Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $462, price is now $236 per person
$236
per person
Dec 6 - Dec 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.
Reviewed on Oct 10, 2025
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.
Reviewed on Oct 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,027, price is now $577 per person
$577
per person
Dec 6 - Dec 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Very clean very nice hotel. Easy accesss to restaurants and shopping.
Reviewed on Oct 11, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,011, price is now $590 per person
$590
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on Oct 4, 2025
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Save 100% on your flight
Price was $697, price is now $411 per person
$411
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
8.2/10 Very Good! (1,006 reviews)
Saturday afternoon pool was busy with families. They have a time for adults 10 - 11pm. I had the gym and pool to myself in the mornings. Gym was open 24/7 and the pool opened at 6 am.
Reviewed on Oct 7, 2025
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Nov 9 to Nov 10
$169 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (3,062 reviews)
"My stay at this hotel was overall pleasant. The staff were professional and welcoming, and the location was convenient for everything I needed. The room was clean, comfortable, and well-maintained, with nice amenities that made the stay enjoyable."
Reviewed on Oct 10, 2025
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Nov 11 to Nov 12
$124 total
Nov 11 - Nov 12
Total with taxes and fees
8.2/10 Very Good! (3,634 reviews)
"Everything was nice, continental breakfast was Great!"
Reviewed on Oct 10, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand, Chicago, IL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $221 total per night from Nov 9 to Nov 10
$221 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (2,177 reviews)
"Great shape!"
Reviewed on Oct 7, 2025
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.
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.
Chicago Children's Museum
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.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
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- Chicago Vacations
- Visit Downtown Chicago
- Navy Pier
- Water Tower Place
- Northwestern Memorial Hospital
- Ohio Street Beach
- John Hancock Center
- Magnificent Mile Vacations
- Michigan Avenue
- Chicago Water Tower
- Ronald McDonald House near Lurie Children’s
- Tribune Tower
- Shops at North Bridge
- Chicago Place Mall
- Prentice Women's Hospital
- Ann and Robert H. Lurie Children's Hospital
- Milton Lee Olive Park
- St. James Cathedral
- Driehaus Museum
- Wrigley Building
- Holy Name Cathedral
- Lookingglass Theatre
- Northwestern Pritzker School of Law
- Downtown Chicago Vacations
- Chinese Consulate
- Michigan Avenue Bridge
- American Medical Association Headquarters
- Chicago Riverwalk
- Chicago Theatre
- Broadway Playhouse
- Seneca Park
- Fourth Presbyterian Church
- 900 North Michigan Shops
- Visit Magnificent Mile
- Visit Chicago
- Marina City
- Museum of Broadcast Communications
- Carbide and Carbon Building
- Rush Street Vacations
- Lake Point Tower
- Oak Street Beach
- Aon Center
- House of Blues Chicago
- Millennium Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.