Near East Side Vacations from ￥389,580

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The Latest Near East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥469,462, price is now ￥389,580 per person
￥389,580
per person
Dec 11 - Dec 17
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
The Riu in Chicago was in a great location downtown. The rooftop bar offered great views, drinks and food. The breakfast buffet was one of the best we've ever had. The room was clean and quiet. You can't ask for more!

Reviewed on Oct 28, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥428,908, price is now ￥391,593 per person
￥391,593
per person
Dec 11 - Dec 17
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥412,869, price is now ￥411,252 per person
￥411,252
per person
Dec 11 - Dec 17
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Breakfast

Reviewed on Oct 27, 2026

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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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

Near East Side Hotel Deals

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 ￥18,413 per night from Nov 26 to Nov 27
￥18,413
￥27,455 total
Nov 26 - Nov 27
includes taxes & fees
9/10 Wonderful! (3,564 reviews)
"You’re paying for the view rooms are old and bathrooms"

Reviewed on Oct 28, 2026

Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥24,887 per night from Nov 22 to Nov 23
￥24,887
￥34,472 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (2,160 reviews)
"Dirty rooms, elevators. They are absolutely not cleaning these rooms thoroughly. Room had used towels in bathroom & uneaten food left in the fridge. They switched us to another room with throw up all over the balcony"

Reviewed on Oct 26, 2026

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 ￥16,456 per night from Nov 22 to Nov 23
￥16,456
￥19,564 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very Good! (10,132 reviews)
"."

Reviewed on Oct 28, 2026

Congress Plaza Hotel
See all 4,610 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 vacation package cost?
Say yes to new adventures with our Near East Side vacation packages, which start from a low ￥389,580. 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 vacation 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 fulfill those vacation 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 vacation?
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 vacation 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 organizing a ritzy city getaway or a budget family adventure, take a look at our vacation packages today.
Can I choose my airline with a Near East Side Expedia vacation 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 vacation package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Locked in your Near East Side vacation 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.

Stay near popular Near East Side attractions

Swissotel Chicago

After visiting Swissotel Chicago, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

￥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.