Addison Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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Addison Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$989, price is now S$696 per person
S$696
per person
17 Oct - 20 Oct
found 10 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,418 reviews)
I think this is a good hotel in an extremely convenient location whether you plan to walk or catch a ride. Close to everything and staff was pleasant.

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,791, price is now S$1,134 per person
S$1,134
per person
17 Oct - 20 Oct
found 10 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,043, price is now S$1,388 per person
S$1,388
per person
17 Oct - 20 Oct
found 10 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,206, price is now S$848 per person
S$848
per person
17 Oct - 20 Oct
found 10 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,382, price is now S$984 per person
S$984
per person
17 Oct - 20 Oct
found 10 hours ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (2,778 reviews)
Property was well located to be able to explore Chicago easily. Very clean hotel and the staff was extremely accommodating. The only thing missing was a pool but it wasn’t a huge issue. Very nice hotel and would go back for sure.

Reviewed on 20 Aug, 2025

Top hotels in Addison

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 S$284 per night from 14 Sept to 15 Sept
S$284
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,965 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on 17 Aug, 2025

Congress Plaza Hotel
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 S$228 per night from 1 Sept to 2 Sept
S$228
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,201 reviews)
"I asked for a microwave and they said they would bring it to the room and it was never delivered, other than that, the stay was very comfortable and convenient."

Reviewed on 18 Aug, 2025

The Wade
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
The price is S$242 per night from 3 Sept to 4 Sept
S$242
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,728 reviews)
"The hotel was wonderfully nestled downtown and an easy walk to sites and restaurants."

Reviewed on 18 Aug, 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Addison

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Addison

Frequently asked questions

How much does an Addison holiday package cost?
Offering great value package deals from S$696 on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday package, consider planning a trip in January, February and November. You'll generally find lower rates on flights and accommodation 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 holiday. 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking accommodation and flights separately. Better still, you can personalise 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 holiday 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 holiday.
How to plan a trip to Addison?

  1. Pick the perfect time to travel: Your schedule, favourite 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.