Logan Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,014 reviews)
Convenient to O’Hare, but the free shuttle did not answer our phone call when we were at the airport needing a ride. From the hotel it was very easy to book it via the front desk.

Reviewed on Jul. 6, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on Jul. 8, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Beautiful!! Location, room, security, everything was perfect! Very classy, elegant!

Reviewed on Jul. 9, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
It’s a great location for walk around the beautiful downtown of Chicago. People were so helpful and friendly. Definitely I’ll consider coming back.

Reviewed on Jul. 7, 2025

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
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

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 $183 per night from Aug 5 to Aug 6
CA $183
CA $215 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,904 reviews)
"Perfect to a short o long stay. Great location if you are planing to visiting Museums, Parks and Iconic places."

Reviewed on Jul. 7, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $278 per night from Aug 10 to Aug 11
CA $278
CA $370 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,992 reviews)
"Great hotel. Near fantastic walkable stops."

Reviewed on Jul. 7, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Aug 10 to Aug 11
CA $233
CA $273 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,406 reviews)
"Everything !!"

Reviewed on Jul. 8, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,674 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 $488. 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.

Discover the most popular places to visit in Logan Square

Busy Beaver Button Museum

You can spend time studying the exhibits at Busy Beaver Button Museum in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Busy Beaver Button Museum

Things to do

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

CA $55
per adult
100% of travellers recommend
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago 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.