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

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

Rp756.150
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp487.755
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

Rp443.676
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

Rp722.600
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.969.085
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

Rp903.250
per adult
94% of travellers recommend
Chicago By Night River and Lake 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 Rp2.838.465 per night from 30 Aug to 31 Aug
Rp2.838.465
Rp3.374.652 total
30 Aug - 31 Aug
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! (10,191 reviews)
"All the staff was very friendly and the room was clean and well maintained. We enjoyed our stay."

Reviewed on 3 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 Rp2.890.909 per night from 17 Aug to 18 Aug
Rp2.890.909
Rp3.437.001 total
17 Aug - 18 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 ...
8/10 Very good! (1,904 reviews)
"Great hotel and in a perfect location"

Reviewed on 3 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is Rp3.045.718 per night from 30 Aug to 31 Aug
Rp3.045.718
Rp3.471.578 total
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 ...
Hyatt Regency O'Hare Chicago
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 Rp4.127.038 per night from 30 Aug to 31 Aug
Rp4.127.038
Rp5.483.339 total
30 Aug - 31 Aug
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 ...
9/10 Wonderful! (2,721 reviews)
"It was our first time touring in Chicago. We are from San Francisco. Loved this hotel! The lobby is beautiful. It has a great restaurant and bar. The staff is very friendly and accommodating. Would definitely stay here again."

Reviewed on 3 Aug 2026

The Allegro Royal Sonesta Hotel Chicago Loop
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundable
The price is Rp3.442.382 per night from 9 Aug to 10 Aug
Rp3.442.382
Rp4.692.600 total
9 Aug - 10 Aug
includes taxes & fees
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the breakfast and the helpful staff ...
Omni Chicago Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is Rp2.610.901 per night from 16 Aug to 17 Aug
Rp2.610.901
Rp3.104.099 total
16 Aug - 17 Aug
includes taxes & fees
Stay at this boutique hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in their ...
7.8/10 Good! (1,878 reviews)
"I stayed to get away for my birthday and although downtown is a bit much. Valet was super easy the vallet driver was extremely friendly. Everything was a 10/10 if I had the patience to deal with downtown traffic I would book here every time"

Reviewed on 3 Aug 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,460 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 Michigan Avenue and Navy Pier 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.

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