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
Price found within the past 48 hours. Click for updated prices.
  • Indoor wedding
    Aug 19 - Aug 22

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,357 reviews)
    "Staff was so helpful"
    Reviewed May 29, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,254
    CA $893
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Smart TV
    Jul 17 - Jul 21

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (490 reviews)
    "Amazing place"
    Reviewed May 26, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,920
    CA $1,274
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Front of property - evening/night
    Aug 10 - Aug 15

    The Peninsula Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    "Everyone was so helpful and friendly Great environment. Cleaning, room service ,breakfast A+"
    Reviewed May 29, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $3,825
    CA $2,676
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • Terrace/patio
    Aug 19 - Aug 22

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

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,512 reviews)
    "Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes."
    Reviewed May 28, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,653
    CA $1,171
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Premium bedding, pillowtop beds, in-room safe, individually furnished
    Jul 31 - Aug 3

    Level Chicago - River North + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,004 reviews)
    "Great room with excellent views!"
    Reviewed May 30, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,877
    CA $1,339
    per traveller
    found 1 day ago
    Level Chicago - River North

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
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jun 29 to Jun 30
CA $180
CA $213 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"

Reviewed on May 29, 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 $261 per night from Jun 30 to Jul 1
CA $261
CA $349 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,288 reviews)
"Staff was super nice and attentive."

Reviewed on May 29, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from Jun 28 to Jun 29
CA $210
CA $249 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,488 reviews)
"rooftop"

Reviewed on May 29, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,765 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 . 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

4.5/5(159 reviews)

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

4.5/5(3 reviews)

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
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(20 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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.