Logan Square Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Aug 13 - Aug 18

    The Westin Chicago Lombard + Flight

    Lombard
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,259 reviews)
    "Requested a room with a walk in shower as I have a broken foot and am wearing a walking boot. Was told none were available but online through the hotels own website it showed they were and were bookable for my entire stay. Rude front desk staff. Probably will never stay there again. This hotel has gone down hill for sure"
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,314
    NZ$2,826
    per traveller
    found 1 day ago
    The Westin Chicago Lombard
  • 55-inch TV with cable channels, video game console, pay films
    Aug 12 - Aug 17

    Hilton Chicago O'Hare Airport + Flight

    O'Hare
    5 nights
    4.0 star property
    8.4/10 - Very good (2,304 reviews)
    "It was a clean room but in AM ready to go in bathroom and who comes out of the bathroom was a large brown cockroach! Yikes!"
    Reviewed May 29, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,056
    NZ$3,237
    per traveller
    found 1 day ago
    Hilton Chicago O'Hare Airport
  • Coffee shop
    Aug 12 - Aug 17

    Hilton Rosemont Chicago O'Hare + Flight

    Rosemont
    5 nights
    3.5 star property
    8.4/10 - Very good (1,000 reviews)
    "Great"
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,302
    NZ$3,509
    per traveller
    found 1 day ago
    Hilton Rosemont Chicago O'Hare
  • Bar (on property)
    Aug 12 - Aug 17

    Embassy Suites by Hilton Chicago O'Hare Rosemont + Flight

    Rosemont
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,396 reviews)
    "Very nice interior in this hotel and I loved my 1 bedroom big unit. There is nice breakfast available and social hour, however bartender was rude. Bathtub was not perfectly clean. No shower handle, only shower head. Overall hotel a little dates but the beds were very comfortable"
    Reviewed May 30, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,674
    NZ$3,097
    per traveller
    found 1 day ago
    Embassy Suites by Hilton Chicago O'Hare Rosemont
  • Exterior
    Aug 12 - Aug 17

    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG + Flight

    Des Plaines
    5 nights
    3.0 star property
    8.8/10 - Excellent (1,855 reviews)
    "Clean and comfortable."
    Reviewed May 30, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,349
    NZ$2,834
    per traveller
    found 1 day ago
    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Our guide on 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

Our pick of the best 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 NZ$252 per night from 29 June to 30 June
NZ$252
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"

Reviewed on 29 May 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 NZ$423 per night from 30 June to 1 July
NZ$423
30 June - 1 July
includes taxes & fees
9.4/10 Exceptional! (4,288 reviews)
"Staff was super nice and attentive."

Reviewed on 29 May 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 NZ$302 per night from 29 June to 30 June
NZ$302
29 June - 30 June
includes taxes & fees
7.8/10 Good! (1,487 reviews)
"rooftop"

Reviewed on 29 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,844 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.

Frequently asked questions

How much does a Logan Square holiday package cost?
Custom make your Logan Square holiday 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 holiday.
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 neighbourhood.
How far in advance should I book my Logan Square holiday?
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 travelling 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 holiday package lets you organise 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 holiday 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 holiday package?
Plans can change in a flash, so yes, you can. You may be able to cancel and rebook your Logan Square holiday 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

Column

Illinois Centennial Memorial Column

Learn about the local history of Chicago with a stop at Illinois Centennial Memorial Column. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.

Illinois Centennial Memorial Column

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.