Stickney Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Stickney
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$160
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$217
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (2,125 reviews)
"Staff were amazing! Extremely helpful and accommodating, let us check in about 5 hours early. Definitely recommend"
Reviewed on 29 Aug, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (880 reviews)
"Check in can be slightly confusing however you get the hang of it quickly. It was close to many amenities, a train away or a longer walk. The loft was cleaning than most however there was still dust and some crumbs left behind. Over all we were pleased with our stay even though very pricey for 3 ..."
Reviewed on 29 Aug, 2026
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.
Stay near popular Stickney attractions
Hawthorne Race Course
You can take time to visit Hawthorne Race Course during your travels to Stickney.
What to do in Stickney
Chicago: Navy Pier Centennial Wheel Ticket
S$32
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend
Frequently asked questions
How much does a Stickney holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Stickney costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Stickney?
If you're looking to score a cheap Stickney holiday package, consider planning a trip in January, February and November. You're likely to find better rates on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Stickney?
Generally, a handful of days is enough to go to the top sights during your Stickney holiday. But if you prefer to have more time to rest or take day trips, think about extending your trip.
How to find the best Stickney package deals?
Start your search for a Stickney package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Stickney package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Stickney getaway off to a flying start.
Is it cheaper to book a Stickney holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can tailor your Stickney escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Stickney?
If you have your Stickney travel dates confirmed, book as soon as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Stickney?
- Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Stickney.
- Set your budget: Consider costs like flights, food and transportation when calculating how much to set aside for your trip to Stickney. Then, choose a property that fits your budget, whether that's a low-cost option or a deluxe getaway.
- Decide how long to go away for: Now that you're more familiar with Stickney, you can figure out the perfect length of your break. Pull together a draft plan and allocate enough time to cover everything you want to see.
- Bundle your accommodation and airfare: Once you've nailed down your travel dates and duration, book the ideal Stickney holiday package for you.
* 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.
