South Addison Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 11 - Jul 13

    The Chicago Hotel Collection Ambassador Gold Coast + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very Good (1,569 reviews)
    "Honestly during my trip I stayed at 6 Chicago hotels and this one was my favorite along with the Midlan hotel. Both exquisite, don’t forget to check out the roof top! I almost left without seeing the view it gorgeous!"
    Reviewed June 8, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    ￥116,174
    ￥99,036
    per traveler
    found 1 day ago
    The Chicago Hotel Collection Ambassador Gold Coast
  • Executive lounge
    Jul 11 - Jul 13

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    8.8/10 - Excellent (2,186 reviews)
    "Clean room, overall nice hotel, restaurant was nice for happy hour. Lobby smelled like an old lady and peltons in gym were broken. Overall lovely stay."
    Reviewed June 9, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    ￥132,393
    ￥109,317
    per traveler
    found 10 hours ago
    Fairmont Chicago at Millennium Park
  • 55-inch TV with cable channels, video-game console, pay movies
    Aug 14 - Aug 20

    Hilton Chicago O'Hare Airport + Flight

    O'Hare
    6 nights
    4.0 star property
    8.4/10 - Very Good (2,329 reviews)
    "Convenience"
    Reviewed June 7, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥440,930
    ￥374,426
    per traveler
    found 18 hours ago
    Hilton Chicago O'Hare Airport
  • Terrace/patio
    Aug 6 - Aug 9

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,888 reviews)
    "Great job"
    Reviewed June 8, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥499,640
    ￥435,238
    per traveler
    found 5 hours ago
    Trump International Hotel & Tower Chicago
  • Lounge
    Aug 6 - Aug 9

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,126 reviews)
    "Staff was amazing. Great hotel and location!"
    Reviewed June 8, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥434,898
    ￥382,073
    per traveler
    found 5 hours ago
    Pendry 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 ￥21,776 per night from Jun 30 to Jul 1
￥21,776
￥25,890 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (10,221 reviews)
"Fantastic room and location."

Reviewed on Jun 9, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ￥25,568 per night from Jul 1 to Jul 2
￥25,568
￥30,396 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,545 reviews)
"Our room was spacious and very clean"

Reviewed on Jun 8, 2026

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥26,396 per night from Jun 29 to Jun 30
￥26,396
￥31,383 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,569 reviews)
"Honestly during my trip I stayed at 6 Chicago hotels and this one was my favorite along with the Midlan hotel. Both exquisite, don’t forget to check out the roof top! I almost left without seeing the view it gorgeous!"

Reviewed on Jun 8, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,679 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.

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

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

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

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

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,276
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,354
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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.