A river with a boat, surrounded by tall buildings and trees.
Photo by Deano
Open Photo by Deano

Near East Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Near East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • An outdoor seating area with a glass table, orange cushions, and potted plants.
    Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,885 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,134
    CA $822
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Dec 9 - Dec 15

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (605 reviews)
    Roundtrip • Vancouver (YVR) - Chicago (ORD)
    YVR - ORD • 1 stop ORD - YVR • 1 stop
    CA $2,039
    CA $1,463
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • A couple dining at a table with a view of a cityscape and a sunset.
    Jan 21 - Jan 24

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,002 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,801
    CA $1,316
    per traveller
    found 2 hours ago
    Park Hyatt Chicago
  • A rooftop lounge with outdoor seating and a city skyline view.
    Jan 21 - Jan 24

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,344
    CA $984
    per traveller
    found 2 hours ago
    Pendry Chicago
  • A street view with outdoor seating, a building with a sign, and tall skyscrapers in the background.
    Dec 17 - Dec 21

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (196 reviews)
    "I’ve stayed at Talbott before and enjoyed it, but this time was pretty disappointing! Towel and amenity services were awful and the shower was very poor pressure."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,148
    CA $850
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection

Where to stay in Near East Side

Find the best Near East Side areas and neighborhoods for the activities you enjoy most.
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
A large, historic building with a central tower and multiple windows, located near a body of water.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Discover the most popular places to visit in Near East Side

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

What to do near Near East Side

360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
See all activities near Near East Side

Near East Side Hotel Deals

A dining table set for six with a cityscape view through large windows.

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Near East Side
9.0 out of 10, Wonderful, (3,580 reviews)
"Had an amazing time celebrating my wife’s birthday I will return ou room was so clean and had all the things that we needed"
The price is CA $183
CA $267 total
includes taxes & fees
Nov 26 - Nov 27
Swissotel - Chicago
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.
See all properties in Near East Side

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 $822. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.