Near 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.
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Where to stay in Near East Side

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

Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is S$253 per night from 24 Nov to 25 Nov
S$253
includes taxes & fees
24 Nov - 25 Nov
8.8/10 Excellent! (1,939 reviews)
"Was clean"

Reviewed on 22 Nov,2024

Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5
221 N Columbus Dr, Chicago, IL
The price is S$237 per night from 15 Dec to 16 Dec
S$237
includes taxes & fees
15 Dec - 16 Dec
8.4/10 Very Good! (1,424 reviews)
"Beautiful hotel in a great location."

Reviewed on 21 Nov,2024

Radisson Blu Aqua Hotel 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 S$135 per night from 28 Nov to 29 Nov
S$135
includes taxes & fees
28 Nov - 29 Nov
7.8/10 Good! (8,142 reviews)
"Ice machines! This was an issue here all summer long. I pointed it out to management over the summer but the issue has gone from bad to worse. Supposedly, there are ice machines on even floors. This visit, housekeeping directed me to the machine on the 4th floor as the only working ice machine. I ..."

Reviewed on 22 Nov,2024

Congress Plaza Hotel
See all 4,045 properties in Near 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 a Near East Side holiday package cost?
Say yes to new adventures with our Near East Side holiday packages, which start from a low . Select the hotels and flights that suit your style. Then, add on a couple of enriching experiences for an unforgettable getaway.
How do I get a cheap travel package to Near East Side?
By bundling. Hotels, rental cars and flights — combine whatever you need into a Near East Side holiday package and save. Score even more bargains when you add extras such as sightseeing tours to your booking. But that’s not the only impressive part. You have the freedom to put together your trip your way. We offer more than 550 airlines and 1,000,000 properties globally, so that everyone has a chance to travel and fulfil those holiday fantasies.
Where should I stay in Near East Side?
Most visitors to Near East Side include both McCormick Place and Millennium Park on their bucket lists. Why not select a hotel within walking distance of these popular attractions?
What are the top hotels in Near East Side?
Book a stay at Swissotel - Chicago. It’s one of this area’s most popular hotels. Another top-rated option in Near East Side is Radisson Blu Aqua Hotel Chicago.
How far in advance should I book my Near East Side holiday?
It’s always wise to book early. Airlines generally release flights up to a year ahead of departure, and this is a great opportunity to land some of the cheapest prices. Boss just told you to use up your holiday time next month? That’s alright! Expedia are never short of fantastic bargains to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Near East Side travel package include?
Car rentals, hotels and flights — we bring you all the best deals. All you’ll have to do is select your preferred combination. After you’ve made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it easy to customize an exciting Near East Side getaway.
What should I know before booking a Near East Side travel package?
You’ll enjoy excellent savings when you bundle your hotels, flights and rental cars into a package. Plus, booking everything in one spot makes trip planning much easier. So why waste your money or time? Whether you’re organising a ritzy city getaway or a budget family adventure, take a look at our holiday packages today.
Can I choose my airline with a Near East Side Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just pick the carrier you want and craft the perfect Near East Side escape.
If I'm not able to travel, can I cancel my Near East Side holiday package?
Whether it’s your hotel, flight or rental car, you can cancel and rebook it. Locked in your Near East Side holiday package in the last 24 hours? You may be able to make changes at no cost. If it’s been longer than that, you may incur a fee from your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We’re here to help you every step of the way.

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

Walking Tour: Holiday Pedway Tour - Limited Time!

Walking Tour: Holiday Pedway Tour - Limited Time!

S$79
Per adult
Walking Tour: Holiday Pedway Tour - Limited Time!
Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$71
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.