East Side Vacations from ￥168,581

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The Latest East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥211,851, price is now ￥168,581 per person
￥168,581
per person
Nov 1 - Nov 4
found 6 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on Sep 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥313,513, price is now ￥224,654 per person
￥224,654
per person
Nov 1 - Nov 4
found 6 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!

Reviewed on Sep 28, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥230,676, price is now ￥179,926 per person
￥179,926
per person
Nov 1 - Nov 4
found 6 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on Sep 29, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥218,872, price is now ￥174,100 per person
￥174,100
per person
Nov 1 - Nov 4
found 6 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay

Reviewed on Sep 19, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥221,998, price is now ￥176,900 per person
￥176,900
per person
Nov 1 - Nov 4
found 6 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Very quiet stay in a noisy city.

Reviewed on Sep 28, 2025

Where to stay in East Side

Find the best East Side areas and neighborhoods for the activities you enjoy most. Learn more about East Side
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 Side 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 ￥20,081 per night from Oct 26 to Oct 27
￥20,081
￥23,573 total
Oct 26 - Oct 27
includes taxes & fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on Sep 25, 2025

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 ￥16,546 per night from Oct 28 to Oct 29
￥16,546
￥22,055 total
Oct 28 - Oct 29
includes taxes & fees
7.8/10 Good! (2,387 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on Sep 24, 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥27,828 per night from Oct 5 to Oct 6
￥27,828
￥32,666 total
Oct 5 - Oct 6
includes taxes & fees
8.4/10 Very Good! (4,998 reviews)
"Lots of food options in the area. If you like to walk, you are close to many shops, Navy Pier, malls and the subway line. The hotel was nice, plenty of food included for breakfast and the happy hour is also nice. Rooms were spacious and everything worked nicely."

Reviewed on Sep 26, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,120 properties in East Side
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 Side vacation package cost?
Our East Side vacation packages, which start from just ￥168,581, are an awesome way to save precious money. Select your preferred hotels, flights and more to create your ideal escape.
How do I get a cheap travel package to East Side?
Bundle your hotels and flights with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your East Side vacation package can be customized exactly to suit your budget. With all that extra money, why not throw in one or two interesting tours and experiences? It's an easy way to unlock even more bargains. That dream vacation to East Side is closer than you thought!
Where should I stay in East Side?
With popular attractions such as Calumet Beach and Calumet Park in this area, look for a hotel positioned near either one. Bronzeville Childrens Museum is another East Side sight that lures the crowds.
How far in advance should I book my East Side vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to East Side sometimes emerge just weeks before departure.
What does an Expedia East Side travel package include?
Car rentals, hotels and flights — we connect you to the very best deals. All you'll have to do is pick and choose your preferred combination. After you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to customize an amazing East Side escape.
What should I know before booking an East Side travel package?
We already have low prices. However, you'll pick up even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.
Can I choose my airline with an East Side 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 take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my East Side vacation package?
Don't stress if you're rethinking your East Side vacation package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realize life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in East Side

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
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

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,144
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,633
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,633
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.