Central Chicago Vacations from ￥262,870
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The Latest Central Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥262,870
per person
Nov 9 - Nov 14
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
We really like Silversmith. We've been there a couple of times. A smaller historical hotel and a bit more personal. We like the Loop! Staff was very good. Susan worked it all out for our group of 4 rooms. Good rooms. Try the "pure wellness" rooms. Quite nice. The attached Adamus restaurant, bar and lounge, was great; breakfast and dinner. The restaurant and bar staff were very attentive and personable! Renee was a fab bertender. Millennium Park and museums are a couple short blocks away. Very good home base to get something done or just explore Chicago.
Reviewed on Aug 29, 2026
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
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.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Streeterville
Navy Pier and Michigan Avenue are just a few worthwhile attractions to visit in Streeterville. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
Near North Side
Navy Pier and Michigan Avenue are a few top attractions in Near North Side. Hop around the city on the metro at Clark-Division Station or Chicago Station (Brown Line) and check out the area's fascinating museums, panoramic lake views, and popular shops.
Find the Best Central Chicago Vacation Packages
Central Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,824
￥20,002 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (10,200 reviews)
"Cool old building with lots of history; however, the room was freezing cold with no ability to adjust the temperature, the water never stayed hot, the bed was firm like a board, and the tub clogged so we were showering with 3 inches of standing water. Regardless, the staff was kind and it did the ..."
Reviewed on Aug 29, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥22,784
￥27,088 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (2,114 reviews)
"Amazing to find an afforable and acceptable place in downtown. Pretty minimal but worth the price."
Reviewed on Aug 29, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (877 reviews)
"The unit was clean, well stocked with everything we needed, and very comfortable! The check in and check out processes were very smooth and the staff’s communications were helpful and friendly."
Reviewed on Aug 28, 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.
Stay near popular Central Chicago attractions
Navy Pier
9.0/10 (24,140 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by © Cesar Russ Photography
McCormick Place
8.8/10 (9,822 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.
Chicago Riverwalk
9.6/10 (13,574 reviews)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
Millennium Park
9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Michigan Avenue
9.4/10 (15,813 reviews)
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.
Grant Park
9.2/10 (12,844 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Art Institute of Chicago
9.4/10 (7,898 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
What to do in Central Chicago
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
Frequently asked questions
How much does a Central Chicago vacation package cost?
Go from wondering to wandering with our Central Chicago vacation packages, which start from just ￥262,870. Pick the flights and hotels that match your travel plans. Then, add on some activities or tours for a one-of-a-kind escape.
How do I get a cheap travel package to Central Chicago?
Browse and lock in everything in one place with our Central Chicago vacation packages. You'll discover bargains on hotels, flights and more that'll keep your travel budget happy and your adventurous spirit full. And, with more than 550 air carriers and 1,000,000 hotels around the globe to choose from, you'll have endless opportunities to mix and match your own way.
Where should I stay in Central Chicago?
A journey to Central Chicago isn't complete without stopping by Wrigley Field and McCormick Place. Stay at a hotel nearby so you can easily access these terrific sights.
What are the top hotels in Central Chicago?
Hilton Garden Inn Chicago Central Loop and Kasa River North Chicago are among the most sought-after properties in Central Chicago. Why not have a look at the rates and facilities at each and then make a decision?
How far in advance should I book my Central Chicago vacation?
Search Expedia to compare international flights as early as possible. You can generally purchase a seat up to a year before departure. If you don't see your preferred carrier, or you've left things to the last moment, don't worry. Cheap fares to Central Chicago sometimes emerge a few weeks before the date of departure.
What does an Expedia Central Chicago travel package include?
Flights, car rentals and hotels — we connect you to the very best deals. All you'll have to do is pick your favorite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an exciting Central Chicago trip.
What should I know before booking a Central Chicago travel package?
You can save big by bundling your hotels, flights and rental cars. Once you've made your booking, you can add on tours and activities. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Central Chicago Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you'd like to fly to Central Chicago in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Central Chicago vacation package?
Because we understand life can be unpredictable, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
