Near East Side Vacation Packages

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Top Holiday Package Deals in Near East Side

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

3.5 out of 5
Save 100% on your flight
per person
Apr. 12 - Apr. 19
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
Loved this property!!

Reviewed on Feb. 22, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,383 reviews)
Great experience!!!!

Reviewed on Mar. 3, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 16 - May 20
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Fantastic stay !!!!! Fantastic location!!!!

Reviewed on Feb. 10, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 29 - Jun. 1
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (998 reviews)
Great location to some of the best Chicago restaurant options

Reviewed on Mar. 3, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 29 - Jun. 1
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8/10 Very Good! (1,433 reviews)
Great location, friendly staff and our room was outstanding. We will stay here again.

Reviewed on Mar. 3, 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 showing a city

Downtown Chicago

4 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

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 CA $240 per night from Mar. 9 to Mar. 10
CA $240
CA $324 total
includes taxes & fees
Mar 9 - Mar 10
8.8/10 Excellent! (1,941 reviews)
"Great location and easy parking option/available. Clean and quiet. Great breakfast at Palm/restaurant as well."

Reviewed on Mar. 1, 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 CA $228 per night from Mar. 23 to Mar. 24
CA $228
CA $312 total
includes taxes & fees
Mar 23 - Mar 24
8.4/10 Very Good! (1,441 reviews)
Bluaqua Chicago
"Amazing as usual"

Reviewed on Feb. 25, 2025

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 CA $166 per night from Mar. 10 to Mar. 11
CA $166
CA $195 total
includes taxes & fees
Mar 10 - Mar 11
7.8/10 Good! (8,560 reviews)
"I"

Reviewed on Mar. 3, 2025

Congress Plaza Hotel
See all 4,218 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 CA $983. 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.

Discover the most popular places to visit in Near East Side

McCormick Place

McCormick Place

4.5/5(141 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 featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Millennium Park featuring autumn colours, street scenes and a city

Millennium Park

4.5/5(722 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

Flyover in Chicago

Flyover in Chicago

CA $54
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $77
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $48
per adult
100% of travellers recommend
Color Factory Chicago Ticket
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.