Streeterville Vacations from $356
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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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $576, price is now $356 per person
$356
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $592, price is now $357 per person
$357
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.
Reviewed on Dec 11, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $613, price is now $373 per person
$373
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $610, price is now $377 per person
$377
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on Dec 4, 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
The price is $95 total per night from Jan 5 to Jan 6
$95 total
per night
Jan 5 - Jan 6
8.8/10 Excellent! (3,469 reviews)
Excellent hôtel, right in the center of town,parking valet or self parking available but expensive as expected. Staff was friendly and super attentive, Cafe restaurant right in the hotel. The best is the hotel is at walking distance to everything downtown also bus available up the street on Michigan ...
Reviewed on Dec 12, 2025
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is $97 total per night from Dec 22 to Dec 23
$97 total
per night
Dec 22 - Dec 23
8.2/10 Very Good! (3,783 reviews)
Wonderful room, great location and friendly helpful staff. The breakfast buffet is really well done.
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
The price is $143 total per night from Jan 6 to Jan 7
$143 total
per night
Jan 6 - Jan 7
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.