Central Chicago Vacations from ￥264,270

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The Latest Central Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥325,356, price is now ￥264,270 per person
￥264,270
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great hotel in a great area. Included breakfast was excellent.

Reviewed on Oct 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥536,132, price is now ￥398,124 per person
￥398,124
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Everything was great

Reviewed on Oct 12, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥423,630, price is now ￥334,191 per person
￥334,191
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Not big fan of the room amenities.

Reviewed on Oct 14, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥431,734, price is now ￥342,454 per person
￥342,454
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant.

Reviewed on Oct 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥346,176, price is now ￥276,322 per person
￥276,322
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

Where to stay in Central Chicago

Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central Chicago
Magnificent Mile - River North

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile

Find the Best Central Chicago Vacation Packages

Central Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,409 reviews)
"Check-in staff: did not know if there were vending machine on each floor. Stated bar was getting ready to close (9p) but actually open until midnight. Room: bedspread…not sure when it was last washed:-( no extra blanket in the closet."

Reviewed on Oct 14, 2025

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Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥10,251 per night from Nov 11 to Nov 12
￥10,251
￥14,716 total
Nov 11 - Nov 12
includes taxes & fees
7.8/10 Good! (2,466 reviews)
"Convenient location with very helpful staff!"

Reviewed on Oct 13, 2025

Freehand Chicago
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 ￥21,882 per night from Nov 9 to Nov 10
￥21,882
￥25,686 total
Nov 9 - Nov 10
includes taxes & fees
8.8/10 Excellent! (3,098 reviews)
"Great"

Reviewed on Oct 14, 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,466 properties in Central Chicago
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.

Discover the most popular places to visit in Central Chicago

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Central Chicago

River tour boat in Chicago

Architecture River Tour

￥7,144
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

￥6,486
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,598
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Central Chicago

Frequently asked questions

Can I cancel my flight booking to Central Chicago due to COVID-19?
In these times of uncertainty, many airlines are offering more flexibility. Click through to our Customer Service Portal to find information about changing or canceling your booking due to COVID-19.
What's the best way to find cheap flights to Central Chicago that have flexible change policies?
Search for your low-cost flights to Central Chicago, then check the "No change fee" box below the "Flexible change policies" subheading. It really is that simple. We get that plans change and flexibility is important, so you can book with confidence with Expedia.
What are some of the general tips for travelers to Central Chicago during the COVID-19 outbreak?
COVID-19 has transformed the world in a profound way, including how we can travel safely. The following tips will help you navigate these new challenges and get you ready for your journey to Central Chicago:
  • Research if any travel restrictions apply to your destination and origin before booking your flight. Also check if there are any requirements you'll have to follow on arrival, such as health testing.
  • Requirements state that you must wear a face mask at the airport, including at security checkpoints. You should be prepared to lower your mask for ID purposes when asked by a TSA employee.
  • Avoid handing your boarding pass (electronic or paper) directly to a TSA officer. Instead, position the pass on the scanner and then hold it up for inspection.
  • You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. You'll have to remove it for screening.
  • Empty your personal items from your pockets, like your wallet and phone, and put them in your carry-on instead of into bins. This will minimize handling during screening.
  • Transport all food items in a clear plastic bag and also put them in a screening bin. Separating food from your carry-on means it's less likely a TSA employee will need to open and touch your bag for inspection.

Which airlines fly to Central Chicago?
Arrange your ticket with American Airlines and then start piecing together your Central Chicago travel agenda. This leading airline runs 13307 flights every month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Central Chicago?
In the last seven days, was the best price for a flight to Central Chicago. If you want to save even more, book well in advance and be flexible with your dates. Search for your trip to Central Chicago, then see prices for similar time frames by clicking on our "flexible dates" link.
How much is a flight to Central Chicago?
One-way flights from () sold for just in the last seven days. During this time, the price of a return ticket to Central Chicago varied between and . If you spot a bargain ticket, book as fast as you can — these prices don't hang about.
What are the most popular airports to fly into in Central Chicago?
Book your flight to O'Hare Intl. Airport (ORD) and sample the best that Central Chicago has to offer. As the region's main entry point, about 33491 flights land here every month.
When is the cheapest time to fly to Central Chicago?
If you'd rather spend your money enjoying Central Chicago rather than on getting there, depart early in the week. The cheapest day to fly is usually Tuesday, with Monday running a close second. With many folks keeping their travel to weekends, Saturday typically has the most expensive airfares.
How much is a plane ticket to Central Chicago?
Fares varied from to in the last seven days. When you're ready to book, we'll be ready to help you land a great deal to Central Chicago.
Which airlines with flights to Central Chicago employ COVID-19 cleanliness policies?
In response to the COVID-19 pandemic, many airlines have implemented extra rules and standards to help travelers fly with peace of mind. Here are some good examples:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.