Old Town Triangle

Chicago

An aerial view of a city with autumn foliage, a river, and a red barn.
A flower shop with various plants and flowers on display.
A vintage street scene with tram tracks, vintage cars, and street signs for W Argyle St, E Goethe St, N Milwaukie Av, N Wells St, and Roosevelt Rd.
A grand hallway with a red brick floor, white columns, and a large chandelier.

Stay near popular Old Town Triangle attractions

A vintage car in a museum exhibit, a neon sign reading "GAS FOR LESS", and a historical mural on the wall.

Chicago History Museum

9.0/10 (37 reviews)
Explore the rich and exciting history of this great, iconic all-American city through an array of artefacts, hands-on exhibits and multi-media presentations.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

S$185
per adult
82% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

S$54
per adult
Chicago Skyline Tiki Chic Party Cruise on Lake Michigan
See all activities in Chicago

Top hotels in Old Town Triangle

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is S$151 per night from 8 Sept to 9 Sept
S$151
8 Sept - 9 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very good! (10,207 reviews)
"Parking was a mess. The parking lot was full and they had to create a space for us to park. The parking lot is also prepay which we didn’t know nor were we told so we were charged a citation for not prepaying and luckily were not towed although three other hotel guests were not so lucky. When I mentioned ..."

Reviewed on 29 Aug, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The price is S$216 per night from 7 Sept to 8 Sept
S$216
7 Sept - 8 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff ...
The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
The price is S$354 per night from 30 Aug to 31 Aug
S$354
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,331 reviews)
"10/10"

Reviewed on 29 Aug, 2026

Hyatt Regency McCormick Place Chicago
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free Wi-Fi, a fitness centre and parking (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (878 reviews)
"We enjoyed our experience. It was clean and quiet and in the heart of the city. A true gem. I cannot wait to return!"

Reviewed on 29 Aug, 2026

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Kasa Magnificent Mile Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is S$293 per night from 7 Sept to 8 Sept
S$293
7 Sept - 8 Sept
includes taxes & fees
Stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a health club. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (3,091 reviews)
"I really enjoyed that they made the BTS ARMY guests feel welcomed"

Reviewed on 29 Aug, 2026

Hilton Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
The price is S$354 per night from 7 Sept to 8 Sept
S$354
7 Sept - 8 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 4 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (3,427 reviews)
"Muy bueno, vista espectacular, buen servicio"

Reviewed on 29 Aug, 2026

Hyatt Regency Chicago
See all 4,459 properties in Old Town Triangle
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.

Where to stay in Old Town Triangle

Find the best Old Town Triangle areas for the activities you enjoy most.
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Old Town Triangle