Old Town Triangle Travel Guide

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)
Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
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

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£82
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

£116
per adult
82% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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 £101 per night from 7 Sept to 8 Sept
£101
7 Sept - 8 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! (10,235 reviews)
"Dont book. This hotel needs to become a museum. Being historic is one thing but having a dirty bathroom with hair all on the towels is another. The AC is a window unit and it blew warm air. The bed was hard as a brick and everything was just way too fragile. Now the ladies at the front desk were ..."

Reviewed on 8 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 £126 per night from 30 Aug to 31 Aug
£126
30 Aug - 31 Aug
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
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is £189 per night from 30 Aug to 31 Aug
£189
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
Hilton Chicago O'Hare Airport
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
The price is £166 per night from 7 Sept to 8 Sept
£166
7 Sept - 8 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and ...
The Allegro Royal Sonesta Hotel Chicago Loop
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 £186 per night from 1 Sept to 2 Sept
£186
1 Sept - 2 Sept
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 ...
Hyatt Regency McCormick Place Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is £143 per night from 30 Aug to 31 Aug
£143
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Rosemont. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.8/10 Excellent! (2,974 reviews)
"Booked a stay last minute when my flight was cancelled. Clean and comfortable room; easy to get something to eat downstairs and the airport shuttle is convenient."

Reviewed on 8 Aug 2026

Hyatt Regency O'Hare Chicago
See all 4,453 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 Lake Michigan 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

Lake Michigan and Michigan Avenue 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.

The Chicago Theatre with illuminated marquee and a wet street reflecting lights.
Photo by Mattyboy876
Open Photo by Mattyboy876

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Old Town Triangle Travel Guide

Choose two or more items and save on your trip: