Old Town Chicago Travel Guide

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 make plans for a show at Second City on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
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Top hotels in Old Town Chicago

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is ₹17,003 per night from 27 Sept to 28 Sept
₹17,003
₹20,214 total
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, room service and a fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (5,466 reviews)
"I had a fantastic stay! The location was perfect—right next to the Hello Kitty Café and directly across from the Trump Hotel, which made for a beautiful view from my room. Everything was clean, comfortable, and overall a great experience. The only downside was that only one elevator was operating ..."

Reviewed on 22 Sept 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ₹17,678 per night from 27 Sept to 28 Sept
₹17,678
₹21,017 total
27 Sept - 28 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! (10,192 reviews)
"I’ve stayed here for years. Every riot"

Reviewed on 22 Sept 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 ₹18,011 per night from 29 Sept to 30 Sept
₹18,011
₹21,413 total
29 Sept - 30 Sept
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
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₹14,801 per night from 30 Sept to 1 Oct
₹14,801
₹17,597 total
30 Sept - 1 Oct
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 ...
The Chicago Hotel Collection - Magnificent Mile
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 ₹18,653 per night from 27 Sept to 28 Sept
₹18,653
₹22,176 total
27 Sept - 28 Sept
includes taxes & fees
Stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free Wi-Fi and valet parking (surcharge). Our guests praise the breakfast and the pool in ...
Hampton Inn Chicago Downtown/Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is ₹17,592 per night from 24 Oct to 25 Oct
₹17,592
₹23,727 total
24 Oct - 25 Oct
includes taxes & fees
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 rooms ...
8.6/10 Excellent! (3,250 reviews)
"Great location, easy access to everything Chicago"

Reviewed on 22 Sept 2026

Hilton Chicago
See all 4,489 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 for the activities you enjoy most.
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

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 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 Travel Guide