Streeterville Vacations from $252
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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 $412, price is now $252 per person
$252
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The room was spotless, the included breakfast was lovely and the staff were very kind.
Reviewed on Dec 10, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $790, price is now $434 per person
$434
per person
Jan 30 - Feb 4
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.
Reviewed on Dec 9, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $632, price is now $393 per person
$393
per person
Feb 14 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Amazing hotel, location, staff, and food!!
Reviewed on Dec 8, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $530, price is now $339 per person
$339
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
This place was amazing !
Reviewed on Dec 9, 2025
La Banque Hotel
Save 100% on your flight
Price was $714, price is now $460 per person
$460
per person
Jan 9 - Jan 12
found 21 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.
Reviewed on Nov 30, 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
$106 nightly
The price is $124 total per night from Dec 17 to Dec 18
$124 total
Dec 17 - Dec 18
Total with taxes and fees
8.8/10 Excellent! (3,456 reviews)
Clean room and friendly staff. We would definitely visit again.
Reviewed on Dec 10, 2025
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $97 total per night from Dec 21 to Dec 22
$97 total
Dec 21 - Dec 22
Total with taxes and fees
8.2/10 Very Good! (3,777 reviews)
Clean spacious room
Reviewed on Dec 10, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand Chicago IL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $147 total per night from Jan 6 to Jan 7
$147 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,267 reviews)
This place was amazing !
Reviewed on Dec 9, 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
4.5/5(834 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
4.5/5(1,913 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 acclaimed art scene.
Chicago Children's Museum
4.5/5(196 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.
Things to do
Chicago Bulls Basketball Game at United Center
$98
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% 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.