South Addison Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 7 - Aug 10

    JW Marriott Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    "Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities "
    Reviewed May 3, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $1,294
    CA $946
    per traveller
    found 16 hours ago
    JW Marriott Chicago
  • Lounge
    Jul 23 - Jul 26

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,126 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,763
    CA $1,251
    per traveller
    found 1 day ago
    Pendry Chicago
  • Premium bedding, pillowtop beds, in-room safe, individually furnished
    Jul 10 - Jul 14

    Level Chicago - River North + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,020 reviews)
    "Great experience and shoutout to the front desk people when I checked in ! They were very accommodating and kind . "
    Reviewed May 20, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,678
    CA $1,200
    per traveller
    found 1 day ago
    Level Chicago - River North
  • Exterior
    Jul 13 - Jul 17

    Hilton Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,802 reviews)
    "Since we have checked in, I have gotten 3 charges! Fees they don't tell you when you check in. I have been charged even after check out and no one is responding."
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,558
    CA $1,118
    per traveller
    found 1 day ago
    Hilton Chicago
  • Terrace/patio
    Jun 26 - Jun 29

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,875 reviews)
    "Great experience! Would stay here agin"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,102
    CA $1,527
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

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

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 $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,171 reviews)
"Good for a sleep and go. Not horrible, certainly not the best hotel i've ever stayed at."

Reviewed on May 20, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 25 to May 26
CA $205
CA $283 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,201 reviews)
"Breakfast bar was very good just need 0to go cups for coffee.I'm"

Reviewed on May 21, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,448 reviews)
"We like the bar area on the top floor. The bar tender was very nice."

Reviewed on May 21, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,714 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 . 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

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.