Central Station Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Central Station

Find the best Central Station areas and neighborhoods for the activities you enjoy most. Learn more about Central Station
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago
A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Top hotels in Central Station

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$208
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (10,183 reviews)
"The security and bell staff were the nicest of the hotel. They were very helpful. The front desk person was not helpful at all. The room was fine and had a nice view. The hallway looked old and smelled like marijuana and cigarettes. The restaurant was not open the entire stay and their was no coffee ..."

Reviewed on 13 Aug, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$218
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,982 reviews)
"Endroit calme, propre et très bien entretenu. Merci à toute l'équipe pour l'accueil !"

Reviewed on 13 Aug, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
S$359
4 Sept - 5 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,423 properties in Central Station
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 Central Station holiday package cost?
Be ready to book, because a trip to Central Station starts from an affordable . When you combine your hotels, flights and car rentals into a travel package, you'll enjoy the lowest prices.
How do I get a cheap travel package to Central Station?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got everything you need. Choose the combination that suits your style and see your savings stack up. We know a package deal is never one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotels from all over the world, which lets you customize your Central Station holiday.
Where should I stay in Central Station?
A trip to Central Station isn't complete without seeing McCormick Place and Millennium Park. Stay somewhere nearby for quick access to these impressive attractions.
How far in advance should I book my Central Station holiday?
Your best bet is to book early. Air carriers usually advertise flight tickets nearly 12 months prior to departure, and this is a perfect opportunity to pick up some rock-bottom prices. Boss just told you to take all your holiday days next month? No problem! Expedia are never short of fantastic deals to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Central Station travel package include?
From airfares and hotels to car rentals, Expedia can help you create a Central Station package that's right for you. Holidaying for a week or two? Give some thought to a flight, rental car and hotel bundle. If you're taking a quick break, an airfare and hotel deal could suit you better. Experiences can also be added once you've made your booking. Our packages make it simple to save and plan.
What should I know before booking a Central Station travel package?
Tailor deals to match your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your escape. You'll save big bucks just by bundling your bookings. Whether you're taking off on a winter snow adventure or relaxing on a sunny beach, your dream holiday is only a few clicks away.
Can I choose my airline with a Central Station Expedia holiday package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Simply select the carrier that suits you and craft the perfect Central Station holiday.
If I'm not able to travel, can I cancel my Central Station holiday package?
Plans can change in a flash, so yes, you can. You may be able to change or cancel your Central Station holiday package at no cost if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your car rental company, airline or hotel may charge additional fees. Want more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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 Chicago

* 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.