Near West Side Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
€777
per person
20 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious
Reviewed on 23 Sept 2026
Where to stay in Near West Side
Find the best Near West Side areas and neighborhoods for the activities you enjoy most. Learn more about Near West 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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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 West Side
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
€211
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (1,225 reviews)
"My family and I had a great stay. Room was clean, friendly staff, good location."
Reviewed on 23 Sept 2026
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
€196
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (2,665 reviews)
"Regina at the front desk was most helpful - she even tolerated me going on and on about going to RiotFest and I am a talker. We very much appreciated the flexibility."
Reviewed on 23 Sept 2026
LIVN - West Loop Chicago
555 West Jackson Boulevard Chicago IL
€166
27 Sept - 28 Sept
includes taxes & fees
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 West Side holiday package cost?
Custom build your Near West Side package from a low €748. Choose from any combination of rental cars, flights and hotels to craft the trip you've been dreaming about for ages. Don't forget to add on a few activities!
How do I get a cheap travel package to Near West Side?
Our Near West Side holiday packages mean plenty of savings for the savvy traveller. For the best deals, simply combine your hotel, flights and extras (including tours) into a convenient package. But great bargains are just the beginning of your next big adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 properties around the world to select from. Whatever your budget, there's a package with your name on it.
Where should I stay in Near West Side?
Make sightseeing a breeze by staying just around the corner from Near West Side's big attractions. University of Illinois Chicago and United Centre are two of the most popular.
What are the top hotels in Near West Side?
If it's your first time in Near West Side, lock in a room at Hyatt House Chicago Medical/University District or Hyatt Place Chicago Medical/University District. Both hotels offer comfortable beds and are favourites among lots of travellers.
How far in advance should I book my Near West Side holiday?
It's difficult to pick the best time for airfares, but we usually say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you're booking late, don't despair. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Near West Side travel package include?
Hotels, flights and a cool set of wheels for your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to creating your Near West Side escape, you're the boss!
What should I know before booking a Near West Side travel package?
A travel package can be easier on the wallet than individually booking all you need for your adventure. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever kind of holiday you're planning, you're bound to find a package that's perfect for you.
Can I choose my airline with a Near West Side Expedia holiday package?
Yes, you're in control. Expedia has access to more than 550 partner airlines around the world, so you can design your Near West Side holiday according to your travel needs.
If I'm not able to travel, can I cancel my Near West Side holiday package?
Because we know life can be unpredictable, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've booked your Near West Side holiday package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
Stay near popular Near West Side attractions
United Center
8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
University of Illinois Chicago
8.4/10 (1,058 reviews)
Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Union Park
After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Credit Union 1 Arena
8.0/10 (5 reviews)
Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
The Old Post Office
You can find out about the history of Chicago with a visit to The Old Post Office. Discover the entertainment choices and notable monuments in this vibrant area.
Maxwell Street Market
You can search for that perfect souvenir at Maxwell Street Market during your stay in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
City Winery
You can make plans for a show at City Winery during your trip to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.
Jane Addams' Hull-House Museum
You can spend time studying the exhibits at Jane Addams' Hull-House Museum in Chicago. Discover the entertainment choices and 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.