Near East Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Near East Side

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Dec. 24 - Dec. 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,559 reviews)
excellent staff, great lounge and location

Reviewed on Nov. 14, 2024

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
per person
Jan. 2 - Jan. 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,005 reviews)
This historic hotel is in the perfect location to visit the city and discover the many bars and restaurants on Chicago’s near north side. It has a nice mix of old and new features, paying homage to the famous Pump Room. Stunning reception. Our room had not really been upgraded to modern standard but the bed was super comfortable. Unfortunately the air conditioning was noisy as was the toilet which was continually running. But it was reasonably priced which made up for it’s shortcomings.

Reviewed on Nov. 3, 2024

The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
per person
Jan. 2 - Jan. 8
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
6.6/10 (685 reviews)
Good and easy communcation with the guest services by phone. No wait time to speak to guest services at all. However, no cheap parking on site, and parking neabry can be expensive also.

Reviewed on Nov. 5, 2024

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec. 23 - Dec. 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely amazing! From the service to the rooms the experience was flawless.

Reviewed on Nov. 11, 2024

The Glen Club

The Glen Club

3.5 out of 5
per person
Jan. 2 - Jan. 8
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (309 reviews)
Beautiful surroundings

Reviewed on Oct. 26, 2024

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

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 hotel + flight trips 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 $189 per night from Nov. 24 to Nov. 25
CA $189
CA $263 total
includes taxes & fees
Nov 24 - Nov 25
8.8/10 Excellent! (1,923 reviews)
"Exquisite"

Reviewed on Nov. 12, 2024

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 $166 per night from Dec. 15 to Dec. 16
CA $166
CA $238 total
includes taxes & fees
Dec 15 - Dec 16
8.4/10 Very Good! (1,433 reviews)
Reliable
"Location was great. Walkable or short uber rides to many sites. Friendly staff. Puzzling shortage of hooks for towels in bath room as well as stinginess in suppling towels. But in general, what you expect from a Radisson."

Reviewed on Nov. 13, 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 CA $120 per night from Nov. 25 to Nov. 26
CA $120
CA $141 total
includes taxes & fees
Nov 25 - Nov 26
7.8/10 Good! (8,066 reviews)
"Every staff member we met greeted us with a smile and were at the ready to answer any questions we had. My son and I were so excited to stay here and we will definitely be back."

Reviewed on Nov. 13, 2024

Congress Plaza Hotel
See all 4,012 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 $672. 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

Image for 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
Image for Wrigley Field

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
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Image for Walking Tour: Holiday Pedway Tour - Limited Time!

Walking Tour: Holiday Pedway Tour - Limited Time!

CA $83
Per adult
Walking Tour: Holiday Pedway Tour - Limited Time!
Image for Flyover in Chicago

Flyover in Chicago

CA $53
Per adult
94% of travellers recommend
Flyover in Chicago
Image for Architecture River Tour

Architecture River Tour

CA $75
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.