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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $907, price is now CA $673 per person
CA $673
per person
Sep 3 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
Always a pleasure and a great location

Reviewed on Jun 24, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,665, price is now CA $1,113 per person
CA $1,113
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Muriel at the front desk made our 54th Anniversary memorable as she upgraded our room to a suite and sent a bottle of Prosecco and box of chocolates to our room plus a voucher for oysters at the restaurant. Kudos to her for being so kind and thoughtful. Thank you so much!!

Reviewed on Jun 30, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,076, price is now CA $779 per person
CA $779
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Nice hotel. Maybe I came at a bad time but there was way more many children than I expected. Not usually a problem but parents sucked and let their kids do whatever in areas with amenities. I paid for a late check out and had multiple house keeping staff knock to ask when I was checking out. Where is the communication in that department? Interior room will leave you with frosted windows and makes it feel a bit like a prison cell so I recommend upgrading for that city view

Reviewed on Jun 29, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,083, price is now CA $798 per person
CA $798
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good.

Reviewed on Jun 30, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was CA $1,045, price is now CA $806 per person
CA $806
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,323 reviews)
Staff were really helpful and sweet during check in. During checkout I was told there are no shuttles to take me to my terminal in quite a short and ubrupt manner. But to be honest the price is ridiculous for the outdated hotel. Seems like they think they can charge Hilton prices for what looks like a motel I the rooms just because they are the only hotel in the airport.

Reviewed on Jun 30, 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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

5 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 refundableReserve now, pay when you stay
The price is CA $242 per night from Jul 1 to Jul 2
CA $242
CA $287 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (2,316 reviews)
"clean room staff was excellent!!!"

Reviewed on Jun 30, 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 refundableReserve now, pay when you stay
The price is CA $224 per night from Jul 7 to Jul 8
CA $224
CA $283 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (1,048 reviews)
"The location was perfect for our visit. One of the doors to a stairwell was locked which I alerted to the staff."

Reviewed on Jun 30, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
The price is CA $386 per night from Jul 26 to Jul 27
CA $386
CA $459 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,323 reviews)
"Clean rooms, great location, helpful staff"

Reviewed on Jun 29, 2026

The Emily Hotel
See all 4,603 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 $673. 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.

Stay near popular Near West Side attractions

A large, modern building with a curved facade and multiple vertical windows.

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 entertainment choices.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture 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.