Near East Side Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 29 - Aug 3

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.2/10 - Very good (2,714 reviews)
    "A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller."
    Reviewed May 22, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €1,670
    €1,016
    per traveller
    found 20 hours ago
    Hotel Felix River North/Magnificent Mile
  • Indoor wedding
    Jul 29 - Aug 3

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,336 reviews)
    "Great location and very convenient to river walk and vicinity."
    Reviewed May 22, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    €2,088
    €1,072
    per traveller
    found 20 hours ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 29 - Aug 3

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,505 reviews)
    "I’m not sure if the hotel had a lack of staff but I called for towels and never received any, the next day they brought towels shortly after I called again."
    Reviewed May 21, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €2,197
    €1,315
    per traveller
    found 20 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 29 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,721 reviews)
    "Great location!"
    Reviewed May 22, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €2,214
    €1,359
    per traveller
    found 20 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 29 - Aug 3

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,876 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €2,250
    €1,436
    per traveller
    found 20 hours ago
    Trump International Hotel & Tower Chicago

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

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

Top hotels in Near East Side

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
The price is €305 per night from 24 May to 25 May
€305
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (3,336 reviews)
"Great location and very convenient to river walk and vicinity."

Reviewed on 22 May 2026

Swissotel - Chicago
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 €137 per night from 25 May to 26 May
€137
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"As one of my first solo trips, I was glad to feel very safe and comfortable during my stay. I had requested and paid extra for a lake front room. On the fourth floor I could barely see the lake, but did face the park. Good news and bad news because the street noise was very loud at times. I ate in ..."

Reviewed on 22 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €187 per night from 27 May to 28 May
€187
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,210 reviews)
"The hotel was marvelous. The breakfasts were amazing. Anything you could think of was there. The rooftop bar is definitely worth visiting."

Reviewed on 22 May 2026

Hotel Riu Plaza Chicago
See all 4,590 properties in Near 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 a Near East Side holiday package cost?
Say yes to new adventures with our Near East Side holiday packages, which start from a low . 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.