East Side 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.
Unlock Black Friday deals

Where to stay in East Side

Find the best East Side areas and neighborhoods for the activities you enjoy most. Learn more about East Side
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 Millennium Park 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 East Side

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$164 per night from 8 Dec to 9 Dec
S$164
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (8,162 reviews)
"Everyone was super nice and they let us check in when we got there even though it was before check in time. Definitely would stay here again"

Reviewed on 27 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$160 per night from 1 Jan to 2 Jan
S$160
includes taxes & fees
1 Jan - 2 Jan,2025
8.6/10 Excellent! (3,571 reviews)
"It was an amazing value for the money!! If definitely go back!"

Reviewed on 29 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$159 per night from 1 Jan to 2 Jan
S$159
includes taxes & fees
1 Jan - 2 Jan,2025
8.4/10 Very Good! (3,252 reviews)
Chicago stay
"This hotel was very clean and the staff were helpful and courteous. I would definitely stay there again. Its conveniently located near most attractions."

Reviewed on 27 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 3,861 properties in East Side
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 an East Side holiday package cost?
Our East Side holiday packages, which start from just , are an awesome way to save precious money. Select your preferred hotels, flights and more to create your ideal escape.
How do I get a cheap travel package to East Side?
Bundle your hotels and flights with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your East Side holiday package can be customized exactly to suit your budget. With all that extra money, why not throw in one or two interesting tours and experiences? It’s an easy way to unlock even more bargains. That dream holiday to East Side is closer than you thought!
Where should I stay in East Side?
With popular attractions such as Calumet Beach and Calumet Park in this area, look for a hotel positioned near either one. Bronzeville Childrens Museum is another East Side sight that lures the crowds.
How far in advance should I book my East Side holiday?
Reserving your spot early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to East Side sometimes emerge just weeks before departure.
What does an Expedia East Side travel package include?
Car rentals, hotels and flights — we connect you to the very best deals. All you’ll have to do is pick and choose your preferred combination. After you’ve made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to customize an amazing East Side escape.
What should I know before booking an East Side travel package?
We already have low prices. However, you’ll pick up even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and tons of choice.
Can I choose my airline with an East Side Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines globally. Our holiday packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my East Side holiday package?
Don’t stress if you’re rethinking your East Side holiday package — you can cancel or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realise life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll take care of it.

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
River tour boat in Chicago

Architecture River Tour

S$65
Per adult
94% of travellers recommend
Architecture River Tour
Private Chicago Scavenger Hunt: Eastside Art Heist

Eastside Chicago The Heist Exploration Game and Tour

S$14
Per adult
Eastside Chicago The Heist Exploration Game and 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.