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Check availability on Streeterville Hotels with Connecting Rooms

Our top choices for Streeterville hotels with connecting rooms

Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2967)
"Great location and great staff!!"
United States
lynne
The price is 1.999.332 ₫
2.347.015 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Aloft Chicago Mag Mile
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1054)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is 2.578.086 ₫
3.798.524 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2266)
"Great staff and restaurants!!"
United States
Abigale
The price is 2.438.070 ₫
3.757.974 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3498)
"Great place to stay "
United States
RaShawna
The price is 2.135.602 ₫
2.506.984 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Chicago/Magnificent Mile Suites
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very good, (3801)
"Comfortable Room, great location and Excellent Staff. "
United States
Charles
The price is 2.013.764 ₫
2.363.956 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
The Whitehall Hotel, BW Premier Collection
Lobby
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2007)
"Great location, clean hotel"
United States
Andre
The price is 2.341.323 ₫
3.366.169 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Millennium Knickerbocker Chicago
Breakfast and lunch served
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1603)
"Great stay!!"
United States
Adrian
The price is 2.571.509 ₫
3.018.695 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Courtyard by Marriott Chicago Magnificent Mile
Pillow-top beds, desk, blackout curtains, iron/ironing board
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1005)
"The room was huge, great stay, clean, convenient, comfortable and great staff. "
United States
Madeline
The price is 2.104.560 ₫
2.470.544 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Meeting facility
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1580)
"Rooms were very nice and staff was great"
United States
Nancy
The price is 3.919.743 ₫
5.390.597 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Sheraton Grand Chicago Riverwalk
Exterior
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1007)
"Everything was amazing!"
United States
Jessica
The price is 2.504.902 ₫
2.940.366 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
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.
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