Near West Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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.
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
Price was CA $1,429, price is now CA $1,057 per person
CA $1,057
per person
Jun 3 - Jun 9
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,318 reviews)
During off season not as many activities

Reviewed on Mar 16, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,311, price is now CA $1,451 per person
CA $1,451
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.

Reviewed on Mar 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,293, price is now CA $1,451 per person
CA $1,451
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Clean room. Very friendly staff

Reviewed on Mar 25, 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 CA $2,347, price is now CA $1,510 per person
CA $1,510
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Rooms are nice, great view, valet parking is great

Reviewed on Mar 24, 2026

Lodge Geneva National

Lodge Geneva National

4 out of 5
Price was CA $1,972, price is now CA $1,404 per person
CA $1,404
per person
Jun 3 - Jun 9
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,366 reviews)
It was ok rooms were noisy can here everything in hall and in next room

Reviewed on Mar 23, 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 showing a city

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

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 CA $264 per night from Apr 5 to Apr 6
CA $264
CA $310 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (1,328 reviews)
Great hotel and close to our dinner reservation.

Reviewed on Mar 23, 2026

The Emily Hotel
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 $172 per night from Mar 29 to Mar 30
CA $172
CA $202 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (2,025 reviews)
First time in Chicago after a long time, will definitely come back to this hotel when I come back

Reviewed on Mar 23, 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 $162 per night from Mar 29 to Mar 30
CA $162
CA $207 total
Mar 29 - Mar 30
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Good lactations.

Reviewed on Mar 24, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
See all 4,711 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 $1,057. 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 fascinating museums.

United Center

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $36
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.