Old Town Chicago, IL

Chicago

A street with outdoor seating, brick buildings, and signs for a barbershop and a restaurant.
A cityscape with a mix of modern and historic architecture, including a prominent red brick building with a green awning and a tall skyscraper in the background.
A wrought iron sign with the inscription 'OLD TOWN' mounted on a building facade.
A black SUV parked in front of a building with red umbrellas and a sign that reads 'Woodie's Flat.'
A mural on a brick building with a sign for 'Corcoran's Grill & Pub' and 'Old Town.'

Stay near popular Old Town Chicago attractions

Second City

9.6/10 (15 reviews)
You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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Old Town Chicago Hotel Deals

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is NT$5,934 per night from Oct 25 to Oct 26
NT$5,934
NT$7,055 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is NT$5,126 per night from Oct 26 to Oct 27
NT$5,126
NT$6,094 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,298 reviews)
"Very comfortable beds.very nice bathroom. AC could be better"

Reviewed on 2026/9/30

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 NT$5,688 per night from Oct 27 to Oct 28
NT$5,688
NT$6,762 total
Oct 27 - Oct 28
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,381 reviews)
"For the location & prestige, the grandeur was all in the external. The room was shabby, the carpet worn & marked (with bleach?) in several places, the amenities were severely lacking (front desk did not even have a sewing kit), staff were running on empty and ragged. Perhaps I had a lot of expectations ..."

Reviewed on 2026/9/30

The Chicago Hotel Collection Ambassador Gold Coast
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
The price is NT$6,462 per night from Oct 15 to Oct 16
NT$6,462
NT$7,682 total
Oct 15 - Oct 16
includes taxes & fees
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,640 reviews)
"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."

Reviewed on 2026/9/29

Hampton Inn Chicago Downtown/Magnificent Mile
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 NT$5,119 per night from Oct 25 to Oct 26
NT$5,119
NT$6,086 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (2,277 reviews)
"Clean room"

Reviewed on 2026/9/30

The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is NT$5,288 per night from Oct 30 to Oct 31
NT$5,288
NT$7,224 total
Oct 30 - Oct 31
includes taxes & fees
Book a 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 ...
8.6/10 Excellent! (3,322 reviews)
"Easy check in/check out, easy and available parking, Friendly and helpful staff, clean and updated room"

Reviewed on 2026/9/30

Hilton Chicago
See all 4,513 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.

Where to stay in Old Town Chicago

Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
Learn more about Old Town Chicago
A cityscape with tall skyscrapers and a historic tower.

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 busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

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.

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 large, historic building with a central tower and multiple windows, located near a body of water.

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 Chicago, IL

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