Old Town Chicago

Chicago

Photo by trenton.badillo
Photo by trenton.badillo
Photo by Marc Jacobs
Photo by Marc Jacobs
Photo by Lisa Frackiewicz
Photo by Lisa Frackiewicz
Photo by Joy Taylor
Photo by Joy Taylor
Photo by Rita Irvine
Photo by Rita Irvine

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Magnificent Mile - River North featuring street scenes, night scenes and signage

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4/5(125 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Soldier Field showing a city, modern architecture and a skyscraper

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

Things to do

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

S$54
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Creepy Cruise

Chicago Creepy Cruise

S$58
per adult
Chicago Creepy Cruise
See all activities in Chicago

Top hotels in Old Town Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$283 per night from 14 Sept to 15 Sept
S$283
14 Sept - 15 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,922 reviews)
"Great hotel overall. Definitely makes you feel back in time, but the bedrooms have a balance of new and old. Although a few hairs were found in the towels, despite being changed daily, I do appreciate how efficient the staff was at keeping all clean and running. Dinning is not the best, but it’s ..."

Reviewed on 15 Aug, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
The price is S$293 per night from 2 Sept to 3 Sept
S$293
2 Sept - 3 Sept
includes taxes & fees
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,856 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on 13 Aug, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
The price is S$229 per night from 25 Aug to 26 Aug
S$229
25 Aug - 26 Aug
includes taxes & fees
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (3,681 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is S$216 per night from 24 Aug to 25 Aug
S$216
24 Aug - 25 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,615 reviews)
"Would have liked complimentary breakfast"

Reviewed on 13 Aug, 2025

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is S$242 per night from 3 Sept to 4 Sept
S$242
3 Sept - 4 Sept
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,708 reviews)
"The Italian restaurant inside is delicious, we went twice! If you aren’t I. The mood for there are so many options that are walkable. The Taco spot around the corner is also a win for food Taco Maya. The only thing we didn’t like is having to wait so long for the elevator, 25 mins to get from the ..."

Reviewed on 15 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
The price is S$210 per night from 2 Sept to 3 Sept
S$210
2 Sept - 3 Sept
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,563 reviews)
"decent bedroom for good night sleep with all the techniques to control the light and window blinds."

Reviewed on 14 Aug, 2025

citizenM Chicago Downtown
See all 4,584 properties in Old Town Chicago
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.

Other neighbourhoods around Old Town Chicago

Chicago which includes a city and modern architecture

Lincoln Park

5/5(5 area reviews)

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.

Lincoln Park
Gold Coast showing street scenes as well as a couple

Gold Coast

The ample dining options and fantastic lake views are top of the list for many visitors to Gold Coast. A stop by Michigan Avenue or Lake Michigan might round out your trip.

Gold Coast
Magnificent Mile - River North featuring street scenes, night scenes and signage

Near North Side

4.5/5(248 area reviews)

Known for its fascinating museums, panoramic lake views and popular shops, there's plenty to explore in Near North Side. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at Clark-Division Station or Chicago Station (Brown Line) to see more of the city.

Near North Side
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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.

River North
Magnificent Mile - River North

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.

Magnificent Mile
Navy Pier which includes general coastal views and wild flowers as well as a couple

Streeterville

Michigan Avenue and Navy Pier are just a few worthwhile attractions to visit in Streeterville. Travellers also love the fascinating museums, panoramic lake views and popular shops.

Streeterville

Old Town Chicago