Near West Side Holidays

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Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,174, price is now €955 per person
€955
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on 5 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,797, price is now €1,400 per person
€1,400
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Incredible everything

Reviewed on 8 May 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was €1,461, price is now €1,156 per person
€1,156
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on 8 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €1,220, price is now €988 per person
€988
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on 6 May 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,158, price is now €966 per person
€966
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
If you’re up for walking, this hotel is a great place to stay close enough to most things.

Reviewed on 8 May 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

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

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 refundable
The price is €136 per night from 25 May to 26 May
€136
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,160 reviews)
👎

Reviewed on 9 May 2026

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundable
The price is €134 per night from 25 May to 26 May
€134
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
..

Reviewed on 9 May 2026

Holiday Inn & Suites Chicago - Downtown by IHG
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
354 North Union Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €225 per night from 25 May to 26 May
€225
25 May - 26 May
includes taxes & fees
9.2/10 Wonderful! (474 reviews)
The rooms were very clean!

Reviewed on 4 May 2026

Level Chicago Fulton Market
See all 4,780 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 €955. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.