Streeterville Vacations from $397

Book a Hotel + Flight or Car together to unlock savings

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.
Palmer House a Hilton Hotel
The Wade
Virgin Hotels Chicago
theWit Chicago, a Hilton Hotel
Arlo Chicago

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville

Streeterville Hotel Deals

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
$150 nightly
The price is $177 total per night from Aug 10 to Aug 11
$177 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul 11, 2025

Hilton Chicago/Magnificent Mile Suites
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
$139 nightly
The price is $163 total per night from Aug 11 to Aug 12
$163 total
Aug 11 - Aug 12
Total includes taxes and fees
8.2/10 Very Good! (3,468 reviews)
"Breakfast is amazing!!! Staff are friendly and helpful. My stay at the Whitehall Hotel was a pleasent one! Thank you!"

Reviewed on Jul 10, 2025

The Whitehall Hotel, BW Premier Collection
The Wade
The Wade
4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $215 total per night from Jul 27 to Jul 28
$215 total
Jul 27 - Jul 28
Total includes taxes and fees
8.2/10 Very Good! (1,076 reviews)
"Nice"

Reviewed on Jul 11, 2025

The Wade
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

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.