Lincoln 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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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Lincoln Square

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $831, price is now CA $598 per person
CA $598
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.

Reviewed on Feb 7, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,469, price is now CA $930 per person
CA $930
per person
Mar 21 - Mar 27
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.

Reviewed on Jan 6, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,424, price is now CA $972 per person
CA $972
per person
Mar 21 - Mar 27
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,301, price is now CA $1,625 per person
CA $1,625
per person
Mar 21 - Mar 27
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Gorgeous property, facilities, and location.

Reviewed on Feb 6, 2026

Where to stay in Lincoln Square

Find the best Lincoln Square areas and neighborhoods for the activities you enjoy most. Learn more about Lincoln Square
Downtown Chicago showing a city

Downtown Chicago

5 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

Lincoln 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 $122 per night from Feb 9 to Feb 10
CA $122
CA $143 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (9,839 reviews)
Great a+++

Reviewed on Feb 1, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Feb 21 to Feb 22
CA $190
CA $263 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,611 reviews)
Yes

Reviewed on Feb 7, 2026

Hilton Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Feb 22 to Feb 23
CA $140
CA $165 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless

Reviewed on Feb 4, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,943 properties in Lincoln 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.
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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 $598. 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.

Discover the most popular places to visit in Lincoln Square

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
96% of travellers recommend
Color Factory Chicago Ticket
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

CA $50
per adult
98% of travellers recommend
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
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.