South Addison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in South Addison

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $851, price is now CA $543 per person
CA $543
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,007 reviews)
This was by far the BEST Hotel!!!

Reviewed on Sep. 1, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug. 31, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was CA $4,082, price is now CA $2,538 per person
CA $2,538
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was CA $1,313, price is now CA $837 per person
CA $837
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,828 reviews)
Great staff and quality of service. Check in process a little confusing and stressful at first but location, amenities, and friendly team made our experience memorable.

Reviewed on Sep. 2, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,906, price is now CA $1,221 per person
CA $1,221
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!

Reviewed on Sep. 2, 2025

Where to stay in South Addison

Find the best South Addison areas and neighborhoods for the activities you enjoy most. Learn more about South Addison
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

South Addison Hotel Deals

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 $176 per night from Sep 4 to Sep 5
CA $176
CA $207 total
Sep 4 - Sep 5
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Sep 22 to Sep 23
CA $252
CA $296 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Sep 22 to Sep 23
CA $230
CA $270 total
Sep 22 - Sep 23
includes taxes & fees
The Wade
See all 4,933 properties in South Addison
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 South Addison vacation package cost?
Handcraft your South Addison package from as low as CA $543. Choose from any combination of flights, hotels and rental cars to put together the escape of your dreams. Be sure to add on some tours and experiences!
How do I get a cheap travel package to South Addison?
It's easy. Just bundle everything together. Hotels, rental cars and flights — combine whatever you need into a South Addison vacation package and save. Score even bigger bargains when you include extras such as day tours to your booking. But that's not the only impressive part. You have the freedom to customize your vacation your way. We offer more than 550 airlines and 1,000,000 hotels around the world, so that everyone has a chance to travel and fulfill those vacation dreams.
How far in advance should I book my South Addison vacation?
To score discount prices, book nice and early. Airlines generally advertise flight tickets, along with some of the lowest fares, nearly 12 months ahead of time. Hotels, experiences and car rental should also be booked early to avoid disappointment. If you've decided on a last-minute getaway in South Addison, there are always lots of great bargains to be had on Expedia. Book something in today!
What does an Expedia South Addison travel package include?
Travel packages include hotels, flights and rental cars, but you can combine any of them to create your dream South Addison trip. You can also add on fun things like activities and experiences once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find anywhere else.
What should I know before booking a South Addison travel package?
A travel package can be customized for your budget and is a terrific way to make your budget go further. How much you include is totally up to you. Rental cars, hotels and flights — come up with a combination that works with your plans.
Can I choose my airline with a South Addison Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you certainly can. Simply pick the airline you want and put together your ideal South Addison getaway.
If I'm not able to travel, can I cancel my South Addison vacation package?
It's hard to predict what the future holds, so it's comforting to know that you can change or cancel your South Addison vacation package. If you made your booking in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in South Addison

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
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
Navy Pier

Navy Pier

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.