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
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$908, price is now S$611 per person
S$611
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
The staff was incredible, they went out of their way to assist and resolve immediately with any issues we had. Marina, Terina, Gazelle, Nicky and the engineer were all great, incuding the cleaning staff. Breakfast and coffee and fruit were fantastic. Will definitely recommend to family and friends and visit again, if we come into the city.

Reviewed on 28 Jun, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,152, price is now S$820 per person
S$820
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.

Reviewed on 28 Jun, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,862, price is now S$1,331 per person
S$1,331
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The Trump hotel is always impeccable and this time was no different. We did bring our newborn (first time parents) and they were beyond accommodating; they provided us a crib.

Reviewed on 28 Jun, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was S$995, price is now S$745 per person
S$745
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,134 reviews)
Room is clean and well appointed. Staff are friendly and helpful. Complimentary happy hour and breakfast are bonus. Above all, the location of this boutique hotel is central and convenient for food and walking to the river front.

Reviewed on 28 Jun, 2026

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was S$987, price is now S$749 per person
S$749
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,047 reviews)
It was an ok stay. Room was clean and the hotel was close to the sites/museums we wanted to see.

Reviewed on 26 Jun, 2026

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

5 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

Top hotels in Central Station

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$210 per night from 30 Jun to 1 Jul
S$210
30 Jun - 1 Jul
includes taxes & fees
8/10 Very good! (10,160 reviews)
"Friendly staff. Encountered a cockroach in the elevator."

Reviewed on 29 Jun, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$278 per night from 5 Jul to 6 Jul
S$278
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,832 reviews)
"Best location on Michigan Avenue"

Reviewed on 27 Jun, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 7 Jul to 8 Jul
S$247
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (4,477 reviews)
"Soooo I paid for the lake view the lake view was not really a lake view the lake is in front of some other buildings I had to have a room change for that reason I appreciated the effort but it was really no difference the carpet in the room looks like it needs to not be there they could do without ..."

Reviewed on 29 Jun, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,443 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 S$611. 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.

* 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.