Logan Square Vacation Packages

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  • Better together

    Save up to CA $4,200 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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Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jun 27 - Jul 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (483 reviews)
    "Perfect stay"
    Reviewed May 20, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,457
    CA $975
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Indoor wedding
    Jul 28 - Aug 2

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,332 reviews)
    "Very good Outstanding service "
    Reviewed May 19, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $3,626
    CA $1,987
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 28 - Aug 2

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

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,507 reviews)
    "The restaurant is awful. The housekeeping service was very good. I had two meals in the restaurant and if the servers weren’t as nice as they were I would have sent them back.,,,,,, I should have sent them back. "
    Reviewed May 19, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,965
    CA $1,891
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 28 - Aug 2

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,713 reviews)
    "Parking was easy. The hotel breakfast and regular menu was really good! Elevators were at times a little inconvenient, but nothing too bad "
    Reviewed May 19, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $3,410
    CA $2,288
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Lobby
    Jul 28 - Aug 2

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.2/10 - Very good (2,706 reviews)
    "The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great! "
    Reviewed May 19, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,379
    CA $1,605
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile

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

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

Logan 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 $184 per night from May 25 to May 26
CA $184
CA $218 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (10,168 reviews)
"I had an amazing view of Lake Michigan and the area but unfortunately Michigan Ave is very noisy at all times of the day and night. In addition, there were no black out shades and due to the rooms facing East, the sunrise was bright and early. I had to buy a sleeping mask just to sleep to 7am. The ..."

Reviewed on May 19, 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 $194 per night from May 25 to May 26
CA $194
CA $270 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,194 reviews)
"Our stay at the Hotel Riu was excellent. The staff was very professional and accommodating. The breakfast buffet had a great selection. The rooftop bar was a great atmosphere. We'll definitely return to stay again."

Reviewed on May 20, 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 refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,439 reviews)
"It was very clean and met standards"

Reviewed on May 20, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,876 properties in Logan 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 Logan Square vacation package cost?
Custom make your Logan Square vacation package from as little as . 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.

Discover the most popular places to visit in Logan Square

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 theater scene in this vibrant area.

Busy Beaver Button Museum

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
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.