Near West Side Vacation Packages

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Top Holiday Package Deals in Near West Side

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 3 - May 6
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Superb service by the staff during our multi-day stay! The shower/water pressure was amazing and we appreciate the replenished water bottles each day. Small cons included a large wine stain to the bed, very noticeable/distracting marker marks to headboard, fraying/unfinished carpet at peripheral edge of the room/wall interface. Overall, I would recommend staying here due to the amazing staff and convenient location!

Reviewed on Mar. 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Beautiful hotel. Great staff. Rooms were amazing!

Reviewed on Mar. 29, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 16 - May 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
Love booking a room there

Reviewed on Mar. 23, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 16 - May 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
The Emily Hotel is a phenomenal place. Leo at the front desk was amazing at checking us in and making our experience so much better. Great stay!! And we look forward to going back for rooftop movie nights!!!

Reviewed on Mar. 23, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 16 - May 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Nice swimming pool for lap swimming.

Reviewed on Mar. 23, 2025

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 showing 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

Near West Side Hotel Deals

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 CA $132 per night from Apr. 6 to Apr. 7
CA $132
CA $155 total
includes taxes & fees
Apr 6 - Apr 7
8.6/10 Excellent! (1,004 reviews)
"People at the front desk were very kind and easy to check in. Room was very nice, clean, and comfortable."

Reviewed on Mar. 25, 2025

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel
The Emily Hotel
4 out of 5
311 North Morgan Street, Chicago, IL
The price is CA $250 per night from Mar. 30 to Mar. 31
CA $250
CA $294 total
includes taxes & fees
Mar 30 - Mar 31
9/10 Wonderful! (1,045 reviews)
"The Emily Hotel is a phenomenal place. Leo at the front desk was amazing at checking us in and making our experience so much better. Great stay!! And we look forward to going back for rooftop movie nights!!!"

Reviewed on Mar. 23, 2025

The Emily Hotel
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 CA $163 per night from Apr. 6 to Apr. 7
CA $163
CA $192 total
includes taxes & fees
Apr 6 - Apr 7
8/10 Very Good! (1,005 reviews)
"The property was as advertised. So often on the internet you see images of a hotel and when you arrive it is not at all what you have seen. In this case we were pleasantly surprised."

Reviewed on Mar. 27, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
See all 4,279 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Near West Side vacation package cost?
Custom build your Near West Side package from a low CA $925. 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 vacation packages mean plenty of savings for the savvy traveler. 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 Center 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 favorites among lots of travelers.
How far in advance should I book my Near West Side vacation?
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 vacation 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 vacation 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 vacation according to your travel needs.
If I'm not able to travel, can I cancel my Near West Side vacation 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 vacation 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.

Discover the most popular places to visit in Near West Side

United Center

United Center

4.5/5(96 reviews)

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
University of Illinois Chicago

University of Illinois Chicago

4/5(32 reviews)

Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.

University of Illinois Chicago

Things to do

Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

CA $55
per adult
Chicago Blackhawks Ice Hockey Game at United Center
The Chicago Helicopter Tour 25 Miles

Chicago Helicopter 25-Mile Tour for up to Three Passengers

CA $934
per traveller
Chicago Helicopter 25-Mile Tour for up to Three Passengers
Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour

Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour

CA $9
per traveller
Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.