East Side Vacations from ₩740,638

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    Save up to ₩1,660,000 when you book a flight and hotel together*

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The Latest East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
Downtown Chicago
Price was ₩892,234, price is now ₩740,638 per person
₩740,638
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
8.8/10 Excellent! (3,598 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ₩1,201,671, price is now ₩851,567 per person
₩851,567
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9/10 Wonderful! (3,502 reviews)
Room was clean and comfortable. Hotel was nice and quiet at night. Bed comfortable. TV options was movies was limited as you have to pay for all movies. Room had no microwave but you could rent one for extra charge. Location and parking was convenient and easy.. staff friendly.

Reviewed on Jul 27, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,037,750, price is now ₩782,676 per person
₩782,676
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
8.2/10 Very Good! (2,854 reviews)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,042,086, price is now ₩823,406 per person
₩823,406
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9/10 Wonderful! (3,725 reviews)
Couldn’t check in but nice

Reviewed on Jul 27, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was ₩1,003,058, price is now ₩832,959 per person
₩832,959
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
8.6/10 Excellent! (3,003 reviews)

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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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 ₩275,751 per night from Aug 10 to Aug 11
₩275,751
₩327,841 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (10,318 reviews)
"First off all I prebooked ahead of time so I wouldn’t have any issues. The day of my check in they weren’t able to find my information and they looked for over 1 hour. I booked 2 rooms and first they claimed only 1 was found. After minutes of going back and forth they found the 2nd room. Both rooms ..."

Reviewed on Jul 27, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩253,720 per night from Aug 9 to Aug 10
₩253,720
₩301,663 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very Good! (1,856 reviews)
"Staff were excellent. Hotel was kind of dingy. Breakfast outrageously expensive."

Reviewed on Jul 26, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩272,848 per night from Aug 9 to Aug 10
₩272,848
₩372,958 total
Aug 9 - Aug 10
includes taxes & fees
Omni Chicago Hotel
See all 4,077 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 ₩740,638, 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.

Stay near popular East Side attractions

Calumet Park

8.0/10 (1 review)
Explore the great outdoors at Calumet Park, a lovely green space in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.