East Side Vacations from NT$29,314

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The Latest East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.2/10 Very Good! (3,512 reviews)
Great location in downtown Chicago but the rooms are a bit outdated.

Reviewed on 2025/8/8

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (1,012 reviews)
Thanks for the food and amazing service

Reviewed on 2025/8/8

ACME Hotel Company

ACME Hotel Company

3.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,739 reviews)
Central and walkable to the Magnificent Mile shopping, Navy Pier, Millenium Park, the Loop and many restaurants. Hotel is older but still comfortable. Parking available next door to hotel (public parking). Cute coffee shop and bakery in lobby and great tasting bar in hotel.

Reviewed on 2025/8/7

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 NT$7,494 per night from Sep 7 to Sep 8
NT$7,494
NT$8,797 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (8,914 reviews)
"I love it"

Reviewed on 2025/8/5

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$5,175 per night from Aug 22 to Aug 23
NT$5,175
NT$6,821 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (1,835 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on 2025/8/8

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$4,579 per night from Aug 24 to Aug 25
NT$4,579
NT$5,376 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (3,640 reviews)
"Close to everything"

Reviewed on 2025/8/9

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,283 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 NT$29,314, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.