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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,184
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on Oct 7, 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.
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.
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.
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 $165
CA $196 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very good! (10,203 reviews)
"When I first walked in to the hotel, I was impressed by the beautiful lobby. But that was it. The rooms are extremely dated, the bathtub has rust all over, and the door frames have huge dents. Yes, they do have nice high ceilings, but the furniture needs to be updated, and the windows need room darkening ..."
Reviewed on Oct 7, 2026
River Hotel
75 East Wacker Drive Chicago IL
CA $237
CA $282 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (5,505 reviews)
"Clean and very helpful staff. Great location!"
Reviewed on Oct 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $203
CA $242 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (2,429 reviews)
"N/A"
Reviewed on Oct 7, 2026
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 $1,184. 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.
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.
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.
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.
Smoke & Mirrors
Smoke & Mirrors 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
Skydeck Chicago at Willis Tower
CA $59
per adult
88% 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.