Addison Vacations from $465

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Your Addison Vacation

Come and experience this amazing city for yourself with a Addison vacation package. Consider spending a few days in the neighborhood of Jefferson Park, which is great for festivals and culture, and your time here will be nothing short of unforgettable. If your trip to Addison includes some sightseeing, check out major attractions such as Oakbrook Center Mall, Edge Ice Arena and Elmhurst College. Whatever your travel plans or the size of your budget, organizing a tailored Addison vacation is a walk in the park with Expedia.

The Latest Addison vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $827, price is now $465 per person
$465
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,621 reviews)
Coffee maker didn’t work.

Reviewed on Aug 22, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $2,464, price is now $1,189 per person
$1,189
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
It is easy to get from the airport to the property by transit 🚇 and walkable to many exciting places like maleficent miles, Navy pier extra and very clean hotel, breakfast is amazing ,staff members incredible amazing.

Reviewed on Aug 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,890, price is now $1,522 per person
$1,522
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug 19, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,565, price is now $840 per person
$840
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
My favorite place to stay , When im in Chicago

Reviewed on Aug 22, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,668, price is now $948 per person
$948
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Boutique hotel in downtown Chicago. Up to date facility, clean, quiet, good location.

Reviewed on Aug 22, 2025

Don't see what you're looking for?
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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

$41
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

$41
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

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Addison

Addison Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,211 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on Aug 20, 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Aug 24 to Aug 25
$168 total
Aug 24 - Aug 25
Total with taxes and fees
7.8/10 Good! (8,982 reviews)
"Experience what it must have felt like to attend the 1893 Worlds Fair"

Reviewed on Aug 22, 2025

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
$152 nightly
The price is $179 total per night from Sep 3 to Sep 4
$179 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,736 reviews)
"Great location for a quick getaway"

Reviewed on Aug 21, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,935 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.

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Frequently asked questions

How much does an Addison vacation package cost?
Offering great value package deals from $465 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?
January, May and December are great times to search for cheap Addison vacation packages. Opting to travel in quieter periods means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Addison?
With a well-planned schedule, you can easily visit the most popular Addison sights in a few days. But if you'd like to discover hidden gems or take day trips, consider booking your Addison vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Addison vacation packages?
Your Addison break is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.