East Village Vacations from ￥309,498

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

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

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The Latest East Village Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥421,916, price is now ￥309,498 per person
￥309,498
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥481,245, price is now ￥312,264 per person
￥312,264
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.

Reviewed on Feb 7, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥579,324, price is now ￥388,004 per person
￥388,004
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥478,193, price is now ￥332,532 per person
￥332,532
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥543,532, price is now ￥396,136 per person
￥396,136
per person
Apr 30 - May 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

Where to stay in East Village

Find the best East Village areas and neighborhoods for the activities you enjoy most. Learn more about East Village
Downtown Chicago showing a city

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

East Village 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
The price is ￥14,032 per night from Feb 9 to Feb 10
￥14,032
￥16,472 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (9,853 reviews)
Friendly staff. Clean room.

Reviewed on Feb 5, 2026

Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,812 per night from Feb 28 to Mar 1
￥30,812
￥36,170 total
Feb 28 - Mar 1
includes taxes & fees
8.2/10 Very Good! (2,210 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.

Reviewed on Feb 2, 2026

Hilton Chicago O'Hare Airport
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,788 per night from Feb 21 to Feb 22
￥21,788
￥30,191 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,610 reviews)
Good

Reviewed on Feb 7, 2026

Hilton Chicago
See all 4,796 properties in East Village
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 an East Village vacation package cost?
Live it up in East Village from as little as ￥309,498. We offer a great selection of hotels, flights and rental cars to suit every budget and style. Pick up even better deals when you add some tours or experiences to your vacation package.
How do I get a cheap travel package to East Village?
Bundle your hotels and flights, throw in extras such as a rental car or activities, and save with an East Village vacation package. You won't just pick up exciting discounts on your escape — you'll have plenty of choice within your reach too. When you book with Expedia, you can choose from more than 550 partner airlines and 1,000,000 properties across the globe. Your next affordable adventure begins right here, right now!
Where should I stay in East Village?
Travelers come from far and wide to experience University of Illinois Chicago and United Center in East Village. Book a room within walking distance of these wonderful attractions to make sightseeing a breeze.
What are the top hotels in East Village?
Ruby Room is one of East Village's top properties. Lock in a room here and you'll be able to sleep soundly knowing you're in excellent hands.
How far in advance should I book my East Village vacation?
Savvy travelers book early. Airlines usually release flight tickets around a year ahead of departure, and this is an ideal opportunity to score some of the cheapest prices. Just been told you should take some vacation time next month? No need to worry. Expedia are never short on fantastic deals to send you on the getaway of your dreams, at an affordable price.
What does an Expedia East Village travel package include?
Expedia has all you need to plan your East Village escape, but what your package looks like is entirely up to you. Select from a combination of rental cars, flights and hotels. Chasing some tours or activities to fill in your time? Once you've made your booking, you can add them on too. No matter your budget, there's a vacation package to suit your needs.
What should I know before booking an East Village travel package?
So many places to visit, so many things to experience. With a travel package, you'll be able to cross more of them off your list. Bundle your flights, hotels and rental cars and enjoy big savings.
Can I choose my airline with an East Village Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my East Village vacation package?
It's hard to predict what the future holds, so it's comforting to know that you can change or cancel your East Village vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.

Discover the most popular places to visit in East Village

Wrigley Field featuring cbd, a sporting event and a city

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(332 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.

Michigan Avenue
Navy Pier featuring a sunset and rides

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

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,883
per adult
88% 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

￥6,341
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

￥6,325
per adult
92% of travellers recommend
Art Institute of Chicago
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.