Chatham Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Where to stay in Chatham

Find the best Chatham areas and neighborhoods for the activities you enjoy most. Learn more about Chatham
Downtown Chicago featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

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.

Find hotels in Downtown Chicago

Top hotels in Chatham

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$158 per night from 10 Dec to 11 Dec
S$158
includes taxes & fees
10 Dec - 11 Dec
7.8/10 Good! (8,182 reviews)
"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled"

Reviewed on 25 Nov,2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$171 per night from 10 Dec to 11 Dec
S$171
includes taxes & fees
10 Dec - 11 Dec
8.6/10 Excellent! (3,552 reviews)
Great stay!
"Great location! Front desk was very helpful in giving some local recommendations."

Reviewed on 26 Nov,2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$162 per night from 28 Nov to 29 Nov
S$162
includes taxes & fees
28 Nov - 29 Nov
8.4/10 Very Good! (3,272 reviews)
"It was a great experience"

Reviewed on 24 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,007 properties in Chatham
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.

Frequently asked questions

How much does a Chatham holiday package cost?
Starting from just , a package is your portal to low-cost travel. Build your own Chatham getaway by choosing from our huge range of hotels, airfares and rental cars.
How do I get a cheap travel package to Chatham?
Imagine all the fun things you could do in Chatham with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your hotel and flights into a Chatham holiday package. You have loads of choice when you book with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 properties around the world. Whether you’re holidaying with the entire family or surprising your special someone, organising a getaway to Chatham is better with a package.
Where should I stay in Chatham?
With fascinating attractions such as Abbott Park and Bronzeville Childrens Museum in this neighbourhood, see if you can find a hotel near them. Advocate Trinity Hospital is another sight that draws the crowds.
How far in advance should I book my Chatham holiday?
Earlier is always better. Airlines generally release flight tickets up to 12 months prior to departure, and this is a great opportunity to pick up some rock-bottom prices. Just been told you need to take some holiday time next month? That’s alright! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Chatham travel package include?
From airfares and hotels to car rentals, Expedia can help you put together a Chatham package that fits you. Heading off for a week or two? Look into a rental car, flight and hotel bundle. If your break is short, a flight and hotel deal may suit you better. Activities can also be added after you’ve booked. Our travel packages make it simple to plan and save.
What should I know before booking a Chatham travel package?
We already have low prices. However, you’ll grab an even better deal if you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and a great range of choice.
Can I choose my airline with a Chatham Expedia holiday package?
Yes, and with more than 550 airlines to choose from around the world, you’re spoiled for choice. Browse the available options and find out which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Chatham holiday package?
You can. We understand that things don’t always go to plan, so we’re here to help if you need to make changes to your Chatham holiday package. It may be possible to change or cancel your itinerary at no cost if you’ve booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Popular places to visit

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
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
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

Things to do

Flyover in Chicago

Flyover in Chicago

S$51
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$60
Per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

S$65
Per adult
94% of travellers recommend
Architecture River Tour
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.