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.
Country Inn & Suites by Radisson, Elgin, IL

Country Inn & Suites by Radisson, Elgin, IL

2.5 out of 5
per person
Mar. 9 - Mar. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8/10 Very Good! (1,001 reviews)
It’s a basic hotel, but it’s comfortable and the beds are comfortable and the shower water pressure is good. Free breakfast everyday. Makes you feel at home

Reviewed on Dec. 30, 2024

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 31 - Apr. 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Property is very nice however it could use a common area and be more inviting in lobby. It seems somewhat stark and cold in lobby. There is nowhere to sit when you walk in but a small side lounge area that is not very inviting.

Reviewed on Jan. 5, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 31 - Apr. 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Chicago Park Hyatt has always been and continues to be a great place to stay in the city's most magnificent neighborhood, North Michigan Avenue. Really happy to see that the staff has a great hospitality spirit, and that the facilities are fresh and perfectly kept. Thank you, Hyatt!

Reviewed on Jan. 4, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 31 - Apr. 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,469 reviews)
Excellent. We will definitely be back!

Reviewed on Jan. 4, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Mar. 1 - Mar. 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,197 reviews)
Good Breakfast, well staffed, nice rooms. Deserves 5 star rating.

Reviewed on Jan. 4, 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

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 Millennium Park 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 $220 per night from Jan. 6 to Jan. 7
CA $220
CA $300 total
includes taxes & fees
Jan 6 - Jan 7
8.8/10 Excellent! (1,933 reviews)
"Exceeded my expectations. Staff is amazing."

Reviewed on Jan. 3, 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 $202 per night from Jan. 12 to Jan. 13
CA $202
CA $281 total
includes taxes & fees
Jan 12 - Jan 13
8.4/10 Very Good! (1,417 reviews)
"Customs service was perfect!"

Reviewed on Jan. 4, 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 $117 per night from Jan. 30 to Jan. 31
CA $117
CA $138 total
includes taxes & fees
Jan 30 - Jan 31
7.8/10 Good! (8,362 reviews)
"Easygoing"

Reviewed on Jan. 4, 2025

Congress Plaza Hotel
See all 4,084 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 $654. 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

Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
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
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

Things to do

Flyover in Chicago

Flyover in Chicago

CA $55
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $70
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $49
per adult
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.