Near East Side Holidays
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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
€4,907
per person
7 Oct - 12 Oct
found 11 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
8.2/10 Very good! (2,960 reviews)
I am very disappointed with this property. The room was small and there were no products in the shower bottles
Never answered when I called front desk
The gentleman at valet was the highlight of this trip
Will not return
Reviewed on 26 Aug 2026
Four Seasons Hotel Chicago
Downtown Chicago
€6,757
per person
7 Oct - 12 Oct
found 11 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on 23 Aug 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
€5,427
per person
7 Oct - 12 Oct
found 11 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)
Well maintained and clean property in that Loop area. Close to plenty of shopping and mass transit. Easy access via the Blue Line from the airport. Friendly ataff. Recommended.
Reviewed on 26 Aug 2026
Freehand Chicago
Downtown Chicago
€5,051
per person
7 Oct - 12 Oct
found 11 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
7.8/10 Good! (3,256 reviews)
I stayed for 10 whole days.
I'll start with the positives. It was serviceable lodging with a comfortable lounge and a friendly bar. The aesthetics were on point, very adorable architecture and interior design. The staff was very friendly and helpful, front desk asisted me a few times and the bar staff were all very warm. The amenities were great, laundry was easy to handle. Location wise, it is in a very lively area downtown. If you aren't used to downtown Chicago, this could be a lot for you. But for me, as someone who loves big cities, it was perfect. Speaking of being used to Chicago, the location is directly on the red line, which was incredibly convenient.
Now for the negatives. Room cleanliness was spotty. Reviews that mention dust have it right, I assume their air moving systems are just old and dirty, so there was always a good amount of dust in the air and on surfaces. Moisture control was a bit of an issue for me aswell because the fan in my bathroom didn't work, but I simply compensated by keeping the windows open while I was away. Personally I never called for housekeeping, but they did seem to move quite slowly when handling other rooms around me. The bedding they use can be a little plasticy
Reviewed on 26 Aug 2026
Where to stay in Near East Side
Find the best Near East Side areas and neighborhoods for the activities you enjoy most. Learn more about Near East Side
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Near East Side
Swissotel - Chicago
323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
€271
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (3,524 reviews)
"Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested. Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary ..."
Reviewed on 26 Aug 2026
Radisson Blu Aqua Hotel Chicago
221 N Columbus Dr Chicago IL
€267
7 Sept - 8 Sept
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€117
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,320 reviews)
"Convenient - right across from Grant Park..."
Reviewed on 26 Aug 2026
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 Near East Side holiday package cost?
Say yes to new adventures with our Near East Side holiday packages, which start from a low €4,907. Select the hotels and flights that suit your style. Then, add on a couple of enriching experiences for an unforgettable getaway.
How do I get a cheap travel package to Near East Side?
By bundling. Hotels, rental cars and flights — combine whatever you need into a Near East Side holiday package and save. Score even more bargains when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the freedom to put together your trip your way. We offer more than 550 airlines and 1,000,000 properties globally, so that everyone has a chance to travel and fulfil those holiday fantasies.
Where should I stay in Near East Side?
Most visitors to Near East Side include both McCormick Place and Millennium Park on their bucket lists. Why not select a hotel within walking distance of these popular attractions?
What are the top hotels in Near East Side?
Book a stay at Swissotel - Chicago. It's one of this area's most popular hotels. Another top-rated option in Near East Side is Radisson Blu Aqua Hotel Chicago.
How far in advance should I book my Near East Side holiday?
It's always wise to book early. Airlines generally release flights up to a year ahead of departure, and this is a great opportunity to land some of the cheapest prices. Boss just told you to use up your holiday time next month? That's alright! Expedia are never short of fantastic bargains to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Near East Side travel package include?
Car rentals, hotels and flights — we bring you all the best deals. All you'll have to do is select your preferred combination. After you've made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it easy to customize an exciting Near East Side getaway.
What should I know before booking a Near East Side travel package?
You'll enjoy excellent savings when you bundle your hotels, flights and rental cars into a package. Plus, booking everything in one spot makes trip planning much easier. So why waste your money or time? Whether you're organising a ritzy city getaway or a budget family adventure, take a look at our holiday packages today.
Can I choose my airline with a Near East Side Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just pick the carrier you want and craft the perfect Near East Side escape.
If I'm not able to travel, can I cancel my Near East Side holiday package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Locked in your Near East Side holiday package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may incur a fee from your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We're here to help you every step of the way.
Stay near popular Near East Side attractions
Swissotel Chicago
After visiting Swissotel Chicago, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.