Logan Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • 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 Logan Square

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,300, price is now CA $993 per person
CA $993
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
There was no one at the desk to let us into the parking garage one evening, had to pay for additional parking nearby. Parking was expensive. Very high tech hotel, makes it secure. Staff was kind. A little less traditional, do not expect a traditional front desk. Great location, great suite!!

Reviewed on Nov 2, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $2,559, price is now CA $1,037 per person
CA $1,037
per person
Dec 19 - Dec 23
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was CA $2,031, price is now CA $1,315 per person
CA $1,315
per person
Dec 24 - Dec 31
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,339, price is now CA $1,641 per person
CA $1,641
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,843, price is now CA $1,417 per person
CA $1,417
per person
Dec 25 - Dec 28
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Had a good stay. Will come again

Reviewed on Nov 2, 2026

Where to stay in Logan Square

Find the best Logan Square areas and neighborhoods for the activities you enjoy most. Learn more about Logan Square
A busy city street with tall buildings, a bus, and cars.

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

Logan Square Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 10 to Nov 11
CA $162
CA $193 total
Nov 10 - Nov 11
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 9 to Nov 10
CA $162
CA $193 total
Nov 9 - Nov 10
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $198 total
Nov 23 - Nov 24
includes taxes & fees
River Hotel
See all 4,851 properties in Logan Square
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 Logan Square vacation package cost?
Custom make your Logan Square vacation package from as little as CA $993. Pick from any combination of rental cars, flights and hotels to create the escape you've been dreaming about. Be sure to add on a few activities!
How do I get a cheap travel package to Logan Square?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we've got it all. Choose the combination that suits your style and watch your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 hotels throughout the world, which lets you customize your Logan Square vacation.
Where should I stay in Logan Square?
Take the hassle out of sightseeing by staying right around the corner from Logan Square's biggest attractions. Wrigley Field and Lincoln Park Zoo are two of the best in this neighborhood.
How far in advance should I book my Logan Square vacation?
Search Expedia to compare international airfares as early as possible. You can usually purchase a seat up to a year in advance. If you don't see your preferred carrier, or you've left things to the last moment, don't worry. Cheap tickets to Logan Square sometimes occur just weeks before the date of departure.
What does an Expedia Logan Square travel package include?
That depends on what you're after. If you're traveling alone, you might decide to combine hotels and flights. Taking the whole family to Logan Square? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Logan Square travel package?
Whether it's adventure or relaxation you're after, a Logan Square vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Logan Square Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you sure can! Just choose the carrier you want and put together the perfect Logan Square getaway.
If I'm not able to travel, can I cancel my Logan Square vacation package?
Plans can change in a flash, so yes, you can. You may be able to cancel and rebook your Logan Square vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may charge a fee. Want more information? Visit our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Stay near popular Logan Square attractions

A train on an elevated track above a pedestrian walkway.

The 606

The 606 is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music and sunsets in the area.
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
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
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.