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.
Delta Hotels by Marriott Chicago Willowbrook

Delta Hotels by Marriott Chicago Willowbrook

3 out of 5
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (429 reviews)
The staff was very friendly. Fast check-in and check-out with no issues! Second time staying here and will stay again!

Reviewed on Jul. 24, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Nice hotel with a great breakfast buffet

Reviewed on Jul. 25, 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)
Large rooms, excellent view and location

Reviewed on Jul. 24, 2025

Hilton Chicago

Hilton 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)
8.4/10 Very Good! (1,986 reviews)
The line to get coffee at the cafe downstairs was always 12 people deep. The staff was not very fast…

Reviewed on Jul. 21, 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
Good building, a little misleading when “separate sitting area” is mentioned in the room, yet the room is still just 2 queen beds and a desk and bench all still in the same room. How is this separate if it’s in the same room? Walkable to downtown with access to everything. Clean enough

Reviewed on Jul. 25, 2025

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 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

Lakeshore East 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 $238 per night from Aug 10 to Aug 11
CA $238
CA $319 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,474 reviews)
"The rooms were great, the view was overlooking the river and Navy Pier. Clean, Quiet, and close to all the main tourist shopping and restaurants downtown."

Reviewed on Jul. 22, 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 $251 per night from Aug 17 to Aug 18
CA $251
CA $336 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 $183 per night from Aug 24 to Aug 25
CA $183
CA $215 total
Aug 24 - Aug 25
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 4,493 properties in Lakeshore East
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 Lakeshore East vacation package cost?
Starting from as low as CA $620, 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.

Discover the most popular places to visit in Lakeshore East

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 Riverwalk and Iconic Architecture Walking Tour

Magnificent Mile Architecture Tour With 360 Chicago Upgrade

CA $45
per adult
Magnificent Mile Architecture Tour With 360 Chicago Upgrade
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.