Addison Vacations from ￥235,424

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The Latest Addison Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
per person
Sep 10 - Sep 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (270 reviews)
walkable to many desireable places.

Reviewed on Jul 16, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
Sep 13 - Sep 20
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (255 reviews)
Great place. Good stay for family vacation to Chicago

Reviewed on Aug 6, 2025

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
per person
Sep 7 - Sep 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (204 reviews)
Perfect location, just outside of downtown. Would recommend and can’t wait to come soon

Reviewed on Aug 5, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 10 - Sep 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,340 reviews)
Great stay…. staff was excellent

Reviewed on Aug 4, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
Sep 13 - Sep 20
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,093 reviews)
The hotel was conveniently located near the airport and was clean. However, the room next door was very loud throughout the night, and the staff did not address the issue. Additionally, the shuttle driver was not very welcoming and had a poor attitude. At $400 a night without breakfast, I believe that's quite overpriced. I would recommend driving a bit further to find a better hotel.

Reviewed on Aug 6, 2025

Find the Best Addison Vacation Packages

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 ￥36,967 per night from Sep 7 to Sep 8
￥36,967
￥43,395 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (8,956 reviews)
"We stayed in a family suite. Both rooms were large. The beds were comfortable."

Reviewed on Aug 4, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥25,528 per night from Sep 4 to Sep 5
￥25,528
￥33,649 total
Sep 4 - Sep 5
includes taxes & fees
8.2/10 Very Good! (1,832 reviews)
"Central location to everything"

Reviewed on Aug 6, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is ￥21,545 per night from Aug 24 to Aug 25
￥21,545
￥25,292 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,351 reviews)
"I liked the in and out parking access for one rate per day."

Reviewed on Aug 6, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,897 properties in 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.

Discover the most popular places to visit in Addison

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

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 featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in Addison

River tour boat in Chicago

Architecture River Tour

￥6,122
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

￥6,646
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

￥4,423
per adult
92% of travellers recommend
Skyline Lake Tour
See all activities in Addison

Frequently asked questions

How much does an Addison vacation package cost?
Offering great value package deals from ￥235,424 on Expedia, you'll be pleasantly surprised at how much a vacation to Addison costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Addison?
If you're hoping to score a cheap Addison vacation package, consider planning a trip in January, February and November. You'll generally find lower rates on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Addison?
Generally, a handful of days is enough to visit the top sights during your Addison vacation. However, if you want to have time to chill out or go on day trips, think about extending your trip.
How to find the best Addison package deals?
Begin your search for an Addison package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Addison package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Addison adventure off to a flying start.
Is it cheaper to book an Addison vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can personalize your Addison getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Addison?
Land fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Addison vacation.
How to plan a trip to Addison?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Addison.
  2. Set a budget: Consider expenses like flights, food and transportation when calculating how much to put aside for your trip to Addison. Then, select a hotel that fits your budget, whether that's an economical option or a lavish retreat.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Addison. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose an Addison vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.