Hometown Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
Hometown Holiday
Our pick of the best Hometown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$248
1 Nov - 2 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
NZ$354
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (5,493 reviews)
"Elevators slow and small and housekeeping is always in them. Housekeeping rude. No lobby store. Rooms small and outdated."
Reviewed on 5 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NZ$303
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,422 reviews)
"The property was in a prime location for access around the city, the staff was friendly and attentive, two things though the housekeeping service didn’t clean my room not once during my stay I stayed for four days, and the bathroom needs ventilation aka a fan. The overall experience was 3.5/5 if ..."
Reviewed on 5 Oct 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.
What to do in Hometown
Skydeck Chicago at Willis Tower
NZ$74
per adult
88% of travellers recommend
Frequently asked questions
How much does a Hometown holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Hometown costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Hometown?
January, February and November are great times to look for cheap Hometown holiday packages. Opting to travel in less busy months means you can typically find lower prices on flights and hotels.
How many days is enough for Hometown?
With a well-planned itinerary, you can easily visit the top Hometown sights in a few days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Hometown holiday for longer.
How to find the best Hometown package deals?
Landing a cheap Hometown package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Hometown package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Hometown holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customised Hometown holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Hometown?
If you've got your Hometown holiday dates confirmed, book early to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Hometown?
- Choose your travel dates: The things you want to do in Hometown and your favourite season can help you decide when to travel.
- Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to airfares and activities. Your hotel will probably be the biggest expense during your trip to Hometown.
- Decide how long to go for: Now that you're up to speed on Hometown, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
- Combine your airfare and accommodation: After you've settled on your dates and duration, lock in the right Hometown 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.
