East Side Vacation Packages
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Top Holiday Package Deals in East Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
CA $1,315
per person
Oct 22 - Oct 26
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
The hotel is in a great area but the hotel itself was okay. Employees were nice and there are two nice bars in the hotel. My main issue is it did not get cold in my room even though I had the thermostat on the coldest setting. Also a bummer that there’s no pool.
Reviewed on Sep 7, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $2,117
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The rooms need to be updated. The room service and bell man took longer than we expected for a Four Seasons. There needs to be someone right when you walk in to direct new guests. We usually stay at the Peninsula Hotel. We wanted to try the Four Seasons but we will go back to the Peninsula Hotel going forward. We got the same type of suite but the bathroom and closet for a family of four was less than desirable. The bar at the hotel had great service! Great selection of upscale bar food. I was very happy about that service! I will say everyone was pleasant and accommodating! The wait times and the lack of attention for need to be compared to the Peninsula.
Reviewed on Sep 7, 2026
Where to stay in East Side
Find the best East Side areas and neighborhoods for the activities you enjoy most. Learn more about East Side
Downtown Chicago
4 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.
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.
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.
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.
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.
East Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $157
CA $186 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,311 reviews)
"Don’t stay here unless you want to stay in a 1980s era hotel where things are falling apart left and right. Had to switch rooms at the beginning because of no warm water or pressure. The next room had warm water but no pressure. It just seems like everything there is falling apart. It smells old ..."
Reviewed on Sep 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $235
CA $280 total
Oct 5 - Oct 6
includes taxes & fees
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (890 reviews)
"Great spot!"
Reviewed on Sep 7, 2026
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.
Frequently asked questions
How much does an East Side vacation package cost?
Our East Side vacation packages, which start from just CA $1,287, are an awesome way to save precious money. Select your preferred hotels, flights and more to create your ideal escape.
How do I get a cheap travel package to East Side?
Bundle your hotels and flights with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your East Side vacation package can be customized exactly to suit your budget. With all that extra money, why not throw in one or two interesting tours and experiences? It's an easy way to unlock even more bargains. That dream vacation to East Side is closer than you thought!
Where should I stay in East Side?
With popular attractions such as Calumet Beach and Calumet Park in this area, look for a hotel positioned near either one. Bronzeville Childrens Museum is another East Side sight that lures the crowds.
How far in advance should I book my East Side vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to East Side sometimes emerge just weeks before departure.
What does an Expedia East Side travel package include?
Car rentals, hotels and flights — we connect you to the very best deals. All you'll have to do is pick and choose your preferred combination. After you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to customize an amazing East Side escape.
What should I know before booking an East Side travel package?
We already have low prices. However, you'll pick up even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.
Can I choose my airline with an East Side Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my East Side vacation package?
Don't stress if you're rethinking your East Side vacation package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realize life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
Stay near popular East Side attractions
Calumet Park
8.0/10 (1 review)
Explore the great outdoors at Calumet Park, a lovely green space in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Calumet Beach
Why not spend a lazy afternoon at Calumet Beach during your trip to Chicago? While you're in the area, wander around the parks.
Munson Beach
Why not spend a lazy afternoon at Munson Beach during your trip to Chicago? While you're in the area, wander around the parks.
Things to do
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.