Near East Side Holidays

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Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,105, price is now S$1,733 per person
S$1,733
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (2,288 reviews)
Chip painting in shower/tub

Reviewed on 22 Aug, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was S$2,898, price is now S$2,234 per person
S$2,234
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Proximity to all gates at airport

Reviewed on 23 Aug, 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
Price was S$2,301, price is now S$1,843 per person
S$1,843
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Not worth the price.

Reviewed on 21 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,224, price is now S$1,802 per person
S$1,802
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,012 reviews)
It was a very nice place. I don’t agree with the parking fees and then the added on three dollar Eco fee when nursing to be parking right beside it that was the cities and didn’t seem like very of secure parking. It wasn’t fenced in or anything just I don’t understand the fee for the parking Other night. It was a stay

Reviewed on 24 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
Price was S$2,181, price is now S$1,844 per person
S$1,844
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (2,393 reviews)
Pool was extremely chlorinated

Reviewed on 24 Aug, 2025

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 which includes a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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
Fully refundableReserve now, pay when you stay
The price is S$276 per night from 1 Sept to 2 Sept
S$276
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (2,656 reviews)
"We love Swissotel. Our room was spacious with a great view. Only complaint was the AC couldn’t get the room cool enough to sleep comfortably. This is our favorite hotel in the city."

Reviewed on 25 Aug, 2025

Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr, Chicago, IL
Fully refundable
The price is S$329 per night from 1 Sept to 2 Sept
S$329
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,633 reviews)
"Nice location. Great pool. Shout out to the bartender, Christian!"

Reviewed on 23 Aug, 2025

Radisson Blu Aqua Hotel Chicago
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 1 Sept to 2 Sept
S$227
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,218 reviews)
"Friendly"

Reviewed on 24 Aug, 2025

The Wade
See all 4,568 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 S$1,733. 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

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
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
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

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

S$45
per adult
Chicago Skyline Tiki Chic Party Cruise on Lake Michigan
Chicago: Tiki Bar Cruise on Chicago River

Chicago: Tiki Bar Cruise on Chicago River or Lake Michigan

S$53
per adult
Chicago: Tiki Bar Cruise on Chicago River or Lake Michigan
Chicago: Chicago River Mimosa n' Bloody Mary Cruise

Chicago: Mimosa n' Bloody Mary Cruise

S$53
per adult
Chicago: Mimosa n' Bloody Mary Cruise
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.