Logan Square Vacation Packages
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Top Holiday Package Deals in Logan Square
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,702
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
They charge a facilities fee which is about 20 bucks a night for the amenities. I generally don't have a problem with that as it includes breakfast. BUT, I was annoyed that in the hotel gym (which isn't bad), the bikes had some problems. It's a slight nitpick, admittedly, but that's what it is. The hotel is very close to transit and the LOOP which is the main area of Chicago. Staff were amazing and helpful, the breakfast was very filling. The gym has weights that go up to 20KG, which is pretty nice and they do have those gymbro slogans on the walls which is kind of fun.
Reviewed on Aug 22, 2026
The Talbott, Autograph Collection
Downtown Chicago
CA $1,447
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
CA $1,265
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.
Reviewed on Aug 21, 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
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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Logan Square Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $142
per night
Sep 8 - Sep 9
8/10 Very good! (10,276 reviews)
"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests ..."
Reviewed on Aug 21, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $197
per night
Aug 23 - Aug 24
8/10 Very good! (2,064 reviews)
"Love the hotel excellent location near by all the main spots of Chicago and has a nice rooftop"
Reviewed on Aug 21, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $345
per night
Sep 11 - Sep 12
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.
Frequently asked questions
How much does a Logan Square vacation package cost?
Custom make your Logan Square vacation package from as little as CA $1,099. 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
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.
Illinois Centennial Memorial Column
Learn about the local history of Chicago when you spend time at Illinois Centennial Memorial Column. Stroll along the lakeside in this vibrant area, or check out its top-notch restaurants.
Concord Music Hall
Concord Music Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Logan Square Farmers Market
You can enjoy retail therapy at Logan Square Farmers Market during your visit to Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.
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 acclaimed art scene in this vibrant area.
Regal City North
You can take time to visit Regal City North during your travels to Chicago. Experience the area's live music and entertainment venues.
Logan Square Auditorium
You can get tickets for a performance at Logan Square Auditorium on your trip to Chicago. Experience the area's live music and entertainment venues.
Rosa's Lounge
Rosa's Lounge 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.