Lincoln Square Vacation Packages

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Top Holiday Package Deals in Lincoln Square

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,444, price is now CA $1,056 per person
CA $1,056
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy. My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.

Reviewed on May 12, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,697, price is now CA $1,134 per person
CA $1,134
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
we didn't have breakfast at the hotel

Reviewed on May 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,716, price is now CA $1,164 per person
CA $1,164
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,958, price is now CA $1,370 per person
CA $1,370
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,548, price is now CA $1,099 per person
CA $1,099
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 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

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
The price is CA $183 per night from May 26 to May 27
CA $183
CA $217 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,219 reviews)
The bar being open late is nice and the staff are very helpful.

Reviewed on May 12, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from May 25 to May 26
CA $204
CA $281 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,120 reviews)
Very happy with this hotel! Would definitely stay here again. The rooftop bar was super cool!

Reviewed on May 12, 2026

Hotel Riu Plaza Chicago
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 $204 per night from May 25 to May 26
CA $204
CA $243 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,301 reviews)
Very nice hotel in a great location.

Reviewed on May 12, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,771 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.
All Inclusive Vacations
All Inclusive Vacations
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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 $1,056. 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

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.