Central Chicago Vacations from ￥358,885

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The Latest Central Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
We have a plenty staying at this hotel has the best locations and restaurant is so good

Reviewed on May 13, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Excellent service!!! Would highly recommend !! I have enjoyed this property many times and will return

Reviewed on May 21, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (977 reviews)
The hotel was absolutely perfect for our quick weekend getaway. It was super comfortable, clean and safe. The staff was wonderful!

Reviewed on May 19, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Had an amazing time! Room cleaners were very sweet and

Reviewed on May 6, 2024

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
Downtown Chicago showing a city

Downtown Chicago

8 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

Central Chicago Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is ￥23,214 per night from May 27 to May 28
￥23,214
per night
May 27 - May 28
7.6/10 Good! (6,777 reviews)
"Looks like old antique hotel. It was quiet and felt very safe."

Reviewed on May 21, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is ￥25,078 per night from May 27 to May 28
￥25,078
per night
May 27 - May 28
8.6/10 Excellent! (2,878 reviews)
Perfect location
"Room was pretty tiny, but manageable. No other complaints. Great location, great staff."

Reviewed on May 21, 2024

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 ￥28,116 per night from May 28 to May 29
￥28,116
per night
May 28 - May 29
8.2/10 Very Good! (1,937 reviews)
"Great service. Guy at front desk was extremely friendly and got us checked in three hours early and gave us a complimentary room upgrade. The room was amazing. It was a corner room with floor to ceiling windows. Great view. The bed was comfortable and the shower is huge with great water pressure. ..."

Reviewed on May 21, 2024

Eurostars Magnificent Mile
See all 1,467 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.

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 ￥358,885. 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.

Discover the most popular places to visit in Central Chicago

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 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
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in Central Chicago

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

￥27,764
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

￥11,048
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Central Chicago

Other vacations you might like

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