Lakeshore East Vacation Packages
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Top Holiday Package Deals in Lakeshore East
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
CA $1,283
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
We were a bit underwhelmed with our stay at The Emily Hotel, especially considering the price. The rooms were very dark, with limited lighting, which made it difficult to get ready. We also found that the hotel was lacking in amenities, which was disappointing given the overall cost of the stay. While the hotel has a stylish aesthetic and a great location, we felt that the experience didn’t quite justify the price. For what you pay, we would have expected brighter, more functional rooms and a few more amenities to make the stay feel worthwhile. Overall, it was fine, but we felt it was expensive for what was offered.
Reviewed on Oct 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,697
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Our stay was fabulous! Curtis, who checked us in (and out), was so helpful with food recommendations and like all staff we encountered, so very nice! Room was impeccably clean and quiet with amazing views! Can’t wait til our next stay
Reviewed on Oct 20, 2026
Where to stay in Lakeshore East
Find the best Lakeshore East areas and neighborhoods for the activities you enjoy most. Learn more about Lakeshore East
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.
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.
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.
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.
Lakeshore East Hotel Deals
Swissotel - Chicago
323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
CA $317
CA $426 total
Oct 25 - Oct 26
includes taxes & fees
9/10 Wonderful! (3,566 reviews)
"The first room I checked in to had the door not flushly closing, and looked like someone had pried their way into the room. I checked in at 2:30am after driving from the Green Bay Packers football game in Green Bay, and they insisted that I check out at 11am. After two or three calls, they managed ..."
Reviewed on Oct 21, 2026
Radisson Blu Aqua Hotel Chicago
221 N Columbus Dr Chicago IL
Fully refundable
CA $333
CA $439 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (2,161 reviews)
"Great hotel very big very luxurious, but do not touch anything in your room or you will be charged. There is no microwave or refrigerator in your room or ice buckets. Lots of unknown charges three to be exact $250 $350 and $ 400 extra unknown charges to my card. We'll see if it's refunded...?"
Reviewed on Oct 20, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $147
CA $175 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (10,176 reviews)
"The room I stayed in 1270 was terrible maintained. It was clean but shower seemed to have be poorly repaired too many times, toilet was loose and a bit crooked, the door nob on the bathroom door coming off, door on the dresser also crooked and tiles on the bathroom floor broken. The hotel does not ..."
Reviewed on Oct 21, 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 a Lakeshore East vacation package cost?
Starting from as low as CA $951, you can handcraft your own Lakeshore East package. Simply combine hotels, flights and rental cars and we'll reward you with discounts.
How do I get a cheap travel package to Lakeshore East?
Just think of all the awesome things you could do in Lakeshore East with a wad of extra cash in your pocket. Watch your savings stack up when you combine your hotel and flights into a Lakeshore East vacation package. You have plenty of choice when you book with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 properties globally. Whether you're taking a vacation with the whole family or traveling with someone special, organizing a trip to Lakeshore East is better with a package.
Where should I stay in Lakeshore East?
Visitors come from all corners of the globe to experience McCormick Place and Millennium Park in Lakeshore East. Stay within a stone's throw of these awesome attractions to make sightseeing a breeze.
What are the top hotels in Lakeshore East?
Swissotel - Chicago and Radisson Blu Aqua Hotel Chicago are two of the most sought-after properties in Lakeshore East. Why not check out the amenities and facilities at each and then decide?
How far in advance should I book my Lakeshore East vacation?
Search Expedia to compare international fares ASAP. You can usually purchase a ticket up to a year in advance. If it's too early for your preferred carrier, or you have to book last minute, fear not. Cheap tickets to Lakeshore East sometimes appear a few weeks before the date of departure.
What does an Expedia Lakeshore East travel package include?
Car rentals, flights and hotels — we connect you to all the best deals. All you'll have to do is pick your favorite combination. Once you've made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it simple to craft an unforgettable Lakeshore East getaway.
What should I know before booking a Lakeshore East travel package?
Locking in all the parts of your getaway together is a smart way to save. Combine your car rentals, airfares and hotels into a convenient little package. But your options don't end at hotels. Expedia has all sorts of properties, including vacation rentals like beachfront villas and city apartments. The list is almost endless!
Can I choose my airline with a Lakeshore East Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you definitely can. Just select your preferred carrier and put together the perfect Lakeshore East vacation.
If I'm not able to travel, can I cancel my Lakeshore East vacation package?
We get that unexpected stuff happens. If you've booked a Lakeshore East vacation package and need to cancel or amend it, we're here to help. It's always worth browsing our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to cancel or amend your itinerary for free. If it's more than 24 hours, your airline, hotel or car rental company may charge a fee.
Stay near popular Lakeshore East attractions
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.
Chicago Park
After visiting Chicago Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Things to do
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
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.