Lincoln Square holiday homes

We found 637 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Lincoln Square that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Lincoln Square

Showing deals for:8 Jan - 15 Jan

Dining
Private kitchen
Room
Exterior detail
Exceptional
(69 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
NZ$5,975
for 7 nights, 1 apartment
NZ$854 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

10% off
NZ$9,114
for 7 nights, 1 home
NZ$1,302 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Interior
Private kitchen
Dining
Interior
Wonderful
(50 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
NZ$6,220
for 7 nights, 1 home
NZ$889 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Exterior
Belmont Harbor
Living area
Private kitchen
Exceptional
(193 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

8% off
NZ$6,585
for 7 nights, 1 home
NZ$941 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Room
Dining
Living area
Living area
Exceptional
(7 reviews)

The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.

Chicago

6% off
NZ$8,553
for 7 nights, 1 apartment
NZ$1,222 per night
includes taxes & fees
The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.
Exterior
Property grounds
Living area
Living area
Exceptional
(109 reviews)

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Chicago

15% off
NZ$2,920
for 7 nights, 1 apartment
NZ$417 per night
includes taxes & fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Interior
Exterior
Dining
Private kitchen
Exceptional
(38 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
NZ$9,557
for 7 nights, 1 apartment
NZ$1,365 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Games room
Living area
Lobby
Games room
Exceptional
(10 reviews)

Elite 4BR Art Deco suite. Garage included.

Chicago

6% off
NZ$6,981
for 7 nights, 1 apartment
NZ$997 per night
includes taxes & fees
Elite 4BR Art Deco suite. Garage included.
Living area
Room
Private kitchen
Living area
Exceptional
(63 reviews)

EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!

Chicago

10% off
NZ$5,829
for 7 nights, 1 apartment
NZ$833 per night
includes taxes & fees
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Dining
Living area
Exterior
Room
Exceptional
(114 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
NZ$9,752
for 7 nights, 1 home
NZ$1,393 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Room
Living area
Kitchen
Interior
Exceptional
(32 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

7% off
NZ$2,801
for 7 nights, 1 apartment
NZ$400 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Private kitchen
Interior
Bathroom
Room
Exceptional
(22 reviews)

Chicago Bear Den

Chicago

7% off
NZ$2,834
for 7 nights, 1 apartment
NZ$405 per night
includes taxes & fees
Chicago Bear Den
Room
Property grounds
Living area
Outdoor dining
Exceptional
(30 reviews)

2BD/1 BA with summer patio in quiet Roscoe Village

Chicago

6% off
NZ$1,769
for 7 nights, 1 apartment
NZ$253 per night
includes taxes & fees
2BD/1 BA with summer patio in quiet Roscoe Village
Terrace/patio
Living area
Private kitchen
Living area
Exceptional
(59 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
NZ$4,474
for 7 nights, 1 apartment
NZ$639 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Bedroom 1 (with Desk)
Side stairwell to Entrance of Unit (see red umbrella on deck)
Private Patio
Living Room
Exceptional
(40 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

8% off
NZ$2,523
for 7 nights, 1 apartment
NZ$360 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Interior
Exterior detail
Room
Dining
Exceptional
(41 reviews)

Stylish Two Bedroom - A block from Wrigley Field

Chicago

7% off
NZ$3,752
for 7 nights, 1 apartment
NZ$536 per night
includes taxes & fees
Stylish Two Bedroom - A block from Wrigley Field
Room
Private kitchen
Exterior detail
Living area
Exceptional
(31 reviews)

Clean & sunny, 2bd, private deck, 15min to Wrigley!

Chicago

7% off
NZ$2,956
for 7 nights, 1 apartment
NZ$422 per night
includes taxes & fees
Clean & sunny, 2bd, private deck, 15min to Wrigley!
Room
Interior
Private kitchen
Interior
Wonderful
(19 reviews)

HIP EAST LAKEVIEW/LINCOLN PARK DESIGNER FLAT

Chicago

6% off
NZ$1,994
for 7 nights, 1 apartment
NZ$285 per night
includes taxes & fees
HIP EAST LAKEVIEW/LINCOLN PARK DESIGNER FLAT
Interior
Living area
Private kitchen
Dining
Wonderful
(156 reviews)

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

Chicago

7% off
NZ$3,805
for 7 nights, 1 apartment
NZ$544 per night
includes taxes & fees
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Meeting facility
Exterior detail
Interior
Living area
Exceptional
(11 reviews)

The Roscoe Village Guesthouse

Chicago

7% off
NZ$2,695
for 7 nights, 1 apartment
NZ$385 per night
includes taxes & fees
The Roscoe Village Guesthouse
Heritage Outpost cafe in lobby
Restored grand lobby with work tables, club seating, and stained glass ceiling
Doorman building with grand lobby
Rooftop lounge leads to roof deck with 360 degree skyline views
Exceptional
(17 reviews)

Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking

Chicago

7% off
NZ$2,038
for 7 nights, 1 apartment
NZ$291 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Room
Interior
Dining
Outdoor dining
Exceptional
(10 reviews)

Wrigleyville Oasis • Modern Comfort Steps from Wrigley Field

Chicago

10% off
NZ$3,317
for 7 nights, 1 apartment
NZ$474 per night
includes taxes & fees
Wrigleyville Oasis • Modern Comfort Steps from Wrigley Field
Exterior
Living area
Living area
Room
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
NZ$5,651
for 7 nights, 1 apartment
NZ$807 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit Lincoln Square for a holiday rental?
The most popular time to visit Lincoln Square is during the peak season from May to July. This vibrant period attracts a diverse crowd, eager to enjoy the lively option and numerous events that the area has to offer. With warm temperatures averaging between 20 to 30 degrees Celsius, visitors can comfortably explore charming local shops, enjoy outdoor dining, and partake in various festivals that celebrate the community's rich culture.July stands out as the peak month, bustling with activity. The long summer days provide ample opportunities for sightseeing and experiencing the local parks, where families gather for picnics and recreational activities. The energy in Lincoln Square during this month is palpable, making it an excellent choice for those looking to soak in the lively spirit of the neighbourhood.For those considering a more budget-friendly option, December is a lovely time to visit Lincoln Square. Although it falls within the low season, this month offers a unique charm as the area transforms with festive decorations and holiday events. Visitors can enjoy a quieter atmosphere while still experiencing the warmth of community gatherings and seasonal celebrations.Ultimately, your choice of when to visit Lincoln Square will depend on whether you prefer the bustling summer energy or the peaceful winter charm.
What are the top attractions in Lincoln Square, Illinois, United States of America?
In Lincoln Square, visitors can enjoy a charming and vibrant setting with various attractions to explore. The neighbourhood is known for its rich German heritage, showcased in its many beer gardens and traditional dining options. The Lincoln Square Farmers Market, held during the warmer months, is a popular spot for fresh produce and local crafts.The area also boasts a picturesque town square, where you can find the iconic Lincoln Square Monument and enjoy seasonal events and festivals. For those interested in arts and culture, the Old Town School of Folk Music offers a variety of concerts and classes, contributing to the neighbourhood's lively arts scene.Additionally, the nearby Riverwalk provides a scenic area for leisurely strolls, with access to parks like the charming Welles Park, where families can enjoy recreational activities.
Are all fees included in the Lincoln Square holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Lincoln Square holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Lincoln Square with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Lincoln Square holiday homes?
You can find great discounts on holiday homes in Lincoln Square on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Lincoln Square holiday home booking on Bookabach?
To find Lincoln Square holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Lincoln Square?
A long-stay holiday home in Lincoln Square is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Lincoln Square holiday home?
Book your Lincoln Square holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Lincoln Square?
Prices for holiday homes in Lincoln Square vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Lincoln Square to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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