Hometown Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Hometown

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$149 per night from 21 Jan to 22 Jan
S$149
includes taxes & fees
21 Jan - 22 Jan
7.8/10 Good! (8,394 reviews)
"My room didn’t have a remote and they never brought it. The bathroom could have been remodeled or something, the tub was old but other than that pretty decent"

Reviewed on 17 Jan,2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$141 per night from 1 Feb to 2 Feb
S$141
includes taxes & fees
1 Feb - 2 Feb
8.6/10 Excellent! (3,719 reviews)
"I enjoyed my stay no complaints ☺️"

Reviewed on 20 Jan,2025

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$150 per night from 18 Feb to 19 Feb
S$150
includes taxes & fees
18 Feb - 19 Feb
8.6/10 Excellent! (2,801 reviews)
"Staycation was very nice. Spa is the absolute best! Service and Ambiance was perfect."

Reviewed on 19 Jan,2025

Eurostars Magnificent Mile
See all 4,132 properties in Hometown
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.

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?

  1. Choose your travel dates: The things you want to do in Hometown and your favourite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. Combine your airfare and accommodation: After you’ve settled on your dates and duration, lock in the right Hometown holiday package for you.

Popular places to visit

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

Wrigley Field

4.5/5(40 reviews)

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

4.5/5(36 reviews)

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

4.5/5(147 reviews)

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 Hometown

Flyover in Chicago

Flyover in Chicago

S$52
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$67
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

S$47
per adult
Color Factory Chicago Ticket
See all activities in Hometown

* 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.