Near West Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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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 featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Near West Side

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.664.112 ₫ per night from 16 Feb to 17 Feb
2.664.112 ₫
3.127.400 ₫ total
16 Feb - 17 Feb
includes taxes & fees
8.8/10 Excellent! (1,950 reviews)
Super helpful, knowledgeable with great communication through text as well. Everything was clean. Wish parking wasn’t so much money :(. The hotel staff went above and beyond for us. Even had a kind man offer to make me a sandwich after the restaurants were closed following a night out. Took the time ...

Reviewed on 6 Feb 2026

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.952.051 ₫ per night from 15 Feb to 16 Feb
3.952.051 ₫
4.639.312 ₫ total
15 Feb - 16 Feb
includes taxes & fees
9/10 Wonderful! (1,301 reviews)
Quiet room for Chicago and amazing neighborhood. And one block away for self parking.

Reviewed on 29 Jan 2026

The Emily Hotel
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
105 N MAY STREET Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.739.104 ₫ per night from 15 Feb to 16 Feb
3.739.104 ₫
4.389.336 ₫ total
15 Feb - 16 Feb
includes taxes & fees
8.8/10 Excellent! (1,177 reviews)
clean room, amenities

Reviewed on 3 Feb 2026

Hyatt House Chicago West Loop
See all 4,994 properties in Near West 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 West Side holiday package cost?
Custom build your Near West Side package from a low . 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 1null000null000 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.

Popular places to visit

Chicago_UnitedCenter_6064077_01

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

United Center
Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

McCormick Place