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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul. 21, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Overall it’s a great hotel.

Reviewed on Jul. 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
First night we went to bed about 11 pm. When we got in bed it was really scratchy. Discovered a bloody mattress pad on top of the sheet below the comforter, see picture attached. The next day, we

Reviewed on Jul. 26, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Great place to stay. Very central to all the fun

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 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

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 CA $220 per night from Aug 10 to Aug 11
CA $220
CA $298 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,496 reviews)
"All around great experience especially the suite view amazing!"

Reviewed on Jul. 25, 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 $252 per night from Aug 17 to Aug 18
CA $252
CA $338 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (1,546 reviews)
"Convenient location"

Reviewed on Jul. 24, 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 $184 per night from Aug 18 to Aug 19
CA $184
CA $216 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,964 reviews)
"The staff was very friendly and helpful"

Reviewed on Jul. 25, 2025

Congress Plaza Hotel
See all 4,540 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
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Beach Vacations
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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 $749. 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

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

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

Michigan Avenue

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

Things to do

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

CA $48
per adult
Chicago Skyline Tiki Chic Party Cruise on Lake Michigan
Walking Tour: Holiday Pedway Tour - Limited Time!

Walking Tour: Underground Chicago via the Pedway

CA $89
per adult
Walking Tour: Underground Chicago via the Pedway
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% 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.