Near West Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by throwingsofas

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Near West Side

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,383, price is now CA $889 per person
CA $889
per person
Jun 5 - Jun 10
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (480 reviews)
The staff was friendly and the bed was very comfortable! Easy to find parking, many food options within walking distance.

Reviewed on Apr 21, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,873, price is now CA $1,261 per person
CA $1,261
per person
Jun 19 - Jun 22
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
I was blown away by our room. So big, clean. Also the 8th floor amenities were amazing! Will definitely be back! Everything about this place was incredible and so clean!

Reviewed on Apr 26, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,812, price is now CA $1,256 per person
CA $1,256
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
We had a great time! Room was clean, spacious, and nice views! Staff was friendly and helpful. Will stay again

Reviewed on Apr 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,254, price is now CA $1,578 per person
CA $1,578
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
Fabulous food and outstanding bar and staff with a phenomenal panoramic view of the heart of Chicago. Love!!!

Reviewed on Apr 27, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,813, price is now CA $1,276 per person
CA $1,276
per person
Jun 10 - Jun 14
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Room was cozy, clean, comfortable! Staff very friendly and in great location

Reviewed on Apr 25, 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

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 $198 per night from May 25 to May 26
CA $198
CA $236 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,126 reviews)
.

Reviewed on Apr 27, 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 CA $179 per night from May 25 to May 26
CA $179
CA $229 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
The room was clean but it had a mildew smell. I hated the shower head and the water was never hot enough. This place was just ok. The location was great!

Reviewed on Apr 26, 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
The price is CA $250 per night from May 10 to May 11
CA $250
CA $328 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (462 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on Apr 25, 2026

Level Chicago Fulton Market
See all 4,830 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 $889. 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

Aerial view of the iconic John Hancock Center and shimmering skyscrapers meeting the tranquil blue of Lake Michigan's shoreline, Chicago, Illinois, United States.

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.