A sign for Lincoln Square with a red brick building in the background.

Lincoln 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

The Latest Lincoln Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,880 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,298
    CA $896
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    Save 100% on your flight
    CA $1,353
    CA $941
    per traveller
    found 1 day ago
    Pendry Chicago
  • Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,012 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    Save 100% on your flight
    CA $1,899
    CA $1,337
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • Dec 29 - Jan 3

    Park Hyatt Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    "This place was amazing and the hotel staff was extremely helpful"
    Reviewed November 10, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • Nonstop
    CA $3,257
    CA $2,340
    per traveller
    found 17 hours ago
    Park Hyatt Chicago
  • Jan 21 - Jan 24

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,783 reviews)
    "Everything was nice. The room was clean and a nice size but it’s the views that make it worthwhile! Waking up & seeing the beautiful sunrise over the lake was amazing!!"
    Reviewed November 11, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,284
    CA $938
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

Where to stay in Lincoln Square

Find the best Lincoln Square areas and neighborhoods for the activities you enjoy most.

Downtown Chicago

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.

What to do near Lincoln Square

Lincoln Square Hotel Deals

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 Lincoln Square vacation package cost?

Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Lincoln Square from just CA $896. And the more you bundle, the more dollars you save. Your dream vacation has never been so affordable.

How do I get a cheap travel package to Lincoln Square?

Our Lincoln Square vacation packages mean plenty of savings for the savvy wanderer. For the best deals, simply combine your hotel, flights and extras (including activities) into an affordable package. But great bargains are just the beginning of your next amazing adventure. Book with Expedia and you'll have more than 550 airlines and 1,000,000 hotel options worldwide to select from. Whatever your style or budget, there's a vacation package here just for you.

Where should I stay in Lincoln Square?

Book a room within walking distance of Lincoln Park, one of this area's top attractions. It's the ideal place for those eager to check out the local sights.

How far in advance should I book my Lincoln Square vacation?

While not all air carriers release tickets early, you can usually start comparing international fares on Expedia up to a year in advance. This is the time you'll bag some fantastic deals. If you've left things to the last minute, you could still be in luck. Low prices occasionally become available just weeks before departure.

What does an Expedia Lincoln Square travel package include?

From flights and hotels to car rentals, Expedia can help you put together a Lincoln Square package that's ideal for you. Heading away for a while? Look into a rental car, flight and hotel bundle. If you're taking a quick break, a hotel and airfare deal could be what you're after. Tours and activities can be added after you've booked. Our vacation packages make it simple to plan and save.

What should I know before booking a Lincoln Square travel package?

Whether it's relaxation or adventure you're chasing, a Lincoln 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 Lincoln Square Expedia vacation package?

Expedia has access to more than 550 airline partners worldwide, so you sure can! Just pick the airline you want and create the perfect Lincoln Square vacation.

If I'm not able to travel, can I cancel my Lincoln Square vacation package?

It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Lincoln Square vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.