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 featuring central business district, a city and a sporting event

Wrigley Field

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 which includes a city, night scenes and signage

Michigan Avenue

You can enjoy some retail therapy 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

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

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 showing modern architecture, autumn leaves and street scenes

Millennium Park

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 skyscraper, a city and modern architecture

Soldier Field

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

P2,411
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

P2,617
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

P2,356
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

P2,443
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

P1,429
per adult
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Creepy Cruise

Chicago Creepy Cruise

P2,617
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 P10,721 per night from Sep 14 to Sep 15
P10,721
P12,585 total
Sep 14 - Sep 15
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! (8,991 reviews)
"Great!"

Reviewed on Aug 19, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
The price is P8,606 per night from Sep 1 to Sep 2
P8,606
P10,103 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,204 reviews)
"Love it"

Reviewed on Aug 19, 2025

The Wade
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 P9,156 per night from Sep 3 to Sep 4
P9,156
P10,749 total
Sep 3 - Sep 4
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! (4,718 reviews)
"We really enjoyed our stay at Embassy suites by Hilton at downtown Chicago. The housekeeping was great and the free breakfast buffet was a plus."

Reviewed on Aug 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
The price is P9,883 per night from Sep 2 to Sep 3
P9,883
P13,027 total
Sep 2 - Sep 3
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! (1,871 reviews)
"It’s a beautiful hotel with lovely staff. The beds were very comfy but the pillows have no neck support. We loved how close it was to Millennium park and how walkable the area was for finding dining options and seeing the sights. It’s only about one city block from the Art Institute and we got to ..."

Reviewed on Aug 18, 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 P8,156 per night from Sep 2 to Sep 3
P8,156
P9,575 total
Sep 2 - Sep 3
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! (3,731 reviews)
"The rooms were beautiful and very well updated. The hotel is only a 20 minute walk from Navy Pier with plenty of great dining options around. The Red Line station is steps from the front door which made everything very accessible."

Reviewed on Aug 18, 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 P9,054 per night from Aug 24 to Aug 25
P9,054
P10,629 total
Aug 24 - Aug 25
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! (2,669 reviews)
"Great location and great staff. Room was super clean and comfortable."

Reviewed on Aug 18, 2025

Hilton Chicago/Magnificent Mile Suites
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

Lincoln Park featuring modern architecture and a city

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.

Lincoln Park
Gold Coast which includes street scenes as well as a couple

Gold Coast

The abundant dining options and 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 which includes a city, night scenes and signage

Near North Side

4.5/5(3 area reviews)

Michigan Avenue and Navy Pier are a few top attractions in Near North Side. Hop around the city on the metro at Clark-Division Station or Chicago Station (Brown Line) and check out the area's fascinating museums, panoramic lake views, and popular shops.

Near North Side
Default Image

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

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

Magnificent Mile
Navy Pier featuring wildflowers and general coastal views as well as a couple

Streeterville

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

Streeterville

Old Town Chicago