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Top Cottage locations in Chicago, IL

South Side Cozy Cottage, welcome home.
  • $89/hr
  • New
  • 5.0 (0)
  • Instant book
  • Responds within 1 hr
  • Chicago, IL
Warm and Cozy Lakeview Cottage
  • $50/hr
  • New
  • 5.0 (3)
  • 3
  • Instant book
  • Responds within 1 hr
  • Portage, IN

How to find Cottage locations in Chicago, IL
Explore Cottage location in Chicago, IL and book your location in minutes.

1. Search

Browse a wide variety of locations or search for specific features

2. Book

Connect with hosts to ask questions and nail down the details

3. Complete

Elevate your next project or event with a unique venue

Frequently Asked Questions about Cottage venues

Do I need my own production or event insurance in Chicago?
Yes. All renters are required to carry Comprehensive Liability and Property Damage insurance with liability coverage of no less than $1,000,000.
What protection plans are available for bookings in Chicago on Giggster?
Giggster offers Damage Protection coverage that you can add to a booking at checkout. Learn more about Giggster's Damage Protection coverage.
What types of locations can I book in Chicago?
You can choose from 42 types! Just search for locations in Chicago at, then click 'Filters' to look for something specific.
How many Cottage locations are available in Chicago?
Right now, there are 366 Cottage locations available in Chicago.
What payment methods does Giggster accept for Chicago bookings?
You can pay for your booking with a credit card, or with ACH or wire transfer for bookings over $4k.
What is the cancellation policy for Chicago guests on Giggster?
Refund options vary, based on when the booking is canceled. Learn more about Giggster's cancellation and refund policy.
What are the cleaning and safety policies for Chicago locations on Giggster?
Now more than ever, your health and safety is our number one priority. We've outlined specific health and safety requirements for both hosts and guests. Learn more about Giggster's COVID-19 Health & Safety Measures.
What locations available near Chicago?
You'll find up to 42 different types of locations in Chicago. Just start a search at and narrow things down with the 'Filter' option.
Is there an extra cost to add more attendees to my Chicago booking?
Yes. Pricing tiers are based on group size. For example, if you booked a space for a group of 1-5 for $30/hr, the price per person is $6/hr. Each additional person would increase the rate by $6/hr.
How much are average location rentals in Chicago?
Rental rates vary with the type and features of the location, but the average rate in Chicago is $69 per hour.
Why should I choose Giggster over other platforms offering rentals in Chicago?
Giggster's got your back — and we know our stuff. Our Customer Support team is knowledgeable and accessible, we offer white glove Select service to help you find the perfect location, and we're experts on the unique needs of production teams.
What is the price range for Cottage locations in Chicago, IL?
Booking prices vary with the property type, features, and rental length, but generally a 1-hour booking will be in the range of $50 to $89.
Which Cottage locations are most popular in Chicago, IL in 2024?
The top 2 Cottage locations in Chicago, IL right now are South Side Cozy Cottage, welcome home. and Warm and Cozy Lakeview Cottage.
How do I book a Chicago location on Giggster?
When you find the right venue, you can connect with the host to get additional info and work out the details. Once everything is all set, you can book and pay for the location in a couple of clicks. Learn more about booking locations.
How do I cancel a Chicago reservation request?
You can contact our team to request a cancellation. Learn more about our cancellation policy.

Have a question about Cottage in Chicago, IL? Ask our City Guides

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Find Cottage locations in Chicago, IL

About Chicago

Known for its stunning skyline and wide array of cultural activities, Chicago is one of the largest cities in the United States. It boasts over 25 miles of lakefront paths to explore, numerous parks, a booming foodie scene, and incredible architecture. Furthermore, Chicago is an excellent destinations because of its access to indie-style cottage events that can’t be found anywhere else.

These events showcase various groups and organizations which bring people together to celebrate music, art, culture, cuisine, and so much more. Popular cottage events include Randolph Street Market Festival and Pitchfork Music Festival.

A fun fact about Chicago is that it was the first American city to have a Skydeck installed on a building – the Sears Tower - allowing visitors to have an unforgettable bird's eye view of this wonderful city. As an interesting fact about this amazing city, Chicago is considered the birthplace of modern skyscraper construction; after all, it was here where the first steel-skeleton skyscraper ever was built!

Cottage Options in Chicago

  • Catering
    When it comes to catering, Chicago has no shortage of great options. From world-famous restaurants to local hidden gems, there is something to suit every taste and budget during your cottage stay.
  • Musicians
    Chicago is home to a wealth of talented musicians, making it the perfect place to find live entertainment for your event.
  • Photography
    If you're looking for a professional photographer to capture your event, Chicago has no shortage of great options.
  • Event Planners
    If you're looking for someone to help plan and execute your event, Chicago has no shortage of great options. From full-service event planning companies to individual consultants, there is sure to be someone who can help make your event a success.

Cottage Vendors in Chicago

  • Stan Mansion
    If you're planning a cottage stay (or even a wedding), you know that the venue is one of the most important elements to consider. After all, it sets the tone for the entire event. The staff at Stan Mansion presents an aura of luxurious grandeur. They curate a space that inspires awe in all guests. The Stan Mansion staff pride themselves on making sure every visitor, from near and far, enjoys the beauty of the space throughout their stay. They understand how much your event means to you, and they're proud to offer a venue that will make it unforgettable.
  • Music by Design
    Music by Design is a DJ service that believes customer service is the key to a successful business. They'll work with you to ensure that your event is everything you've ever dreamed of - from consulting to determining the best music for your day to organization and planning. At the same time, they'll also take your input into consideration to ensure that your cottage stay is truly one-of-a-kind.
  • Events by Abby
    Whether you’re planning a small gathering or a grand affair, details matter. As a professional event planner, Abby has the knowledge and expertise to make sure your event goes off without a hitch. But she also understands that today’s couples are often working with a tight budget. That’s why she offers affordable, comprehensive event packages that will give you peace of mind on your big day. From set-up to clean-up, she’ll take care of everything so you can relax and enjoy your event. And in the rare case that something does go wrong, you can rest assured knowing that she's prepared to handle any situation.

Pros and Cons of Cottage Events in Chicago

While every city has its pros and cons, Chicago is a great place to live for a variety of reasons. The city offers a wealth of cultural attractions, a rich history, and a vibrant nightlife scene. However, it's important to be aware of the potential downsides of living in Chicago before making the move.


  • Wide variety of cultural attractions.

  • A rich history and vibrant nightlife scene.

  • Access to indie-style cottage events.

  • Opportunities for catering, music, and event planning services.

  • Easily accessible waterfront paths and parks.


  • Congested traffic in certain areas.

  • Higher levels of pollution due to large city size.

  • Risk of extreme weather conditions like snowstorms and tornadoes.

  • Higher crime rates compared to other cities.

  • Limited green space in some areas.

Tips on How to Organize Cottage Events in Chicago

The best way to enjoy all that Chicago has to offer is to stay in a cottage. Visiting the many great and unique cottages in the Chicago area can be a great way to capture some of the city's beauty. Here are some tips on how to organize your cottage rental in Chicago:

  • To efficiently organize which cottages you visit, start by researching some options on the internet. Make sure to read reviews so you can get an idea of what locations may best fit your needs.

  • Additionally, if possible, talk to friends or family who have visited area cottages and can offer expert advice – they may have firsthand experience that could really help narrow down your choices.

  • Once you've selected a few contenders, create an itinerary for your day trip that allows enough time to stop and explore each destination without feeling rushed.

  • Finally, for even more added convenience, look into renting a car so that you don't need to rely on public transportation – this makes it easy to go from one spot to another without waiting for connections.

Famous Locations in Chicago

  • 875 North Michigan
    If you're looking for a breathtaking view of Chicago, The Tilt is definitely the place to go. Not only will you get an up-close and personal view of the city skyline, but you'll also be treated to a heart-pounding thrill ride as you're tilted outwards on an enclosed glass and steel platform. And if that's not enough to get your adrenaline going, there's also a café and bar where you can relax with a craft beer or cocktail.
  • Adler Planetarium
    Adler Planetarium, which opened in 1930 and is located on Chicago's Northerly Island's northernmost point, is a vast scientific facility. Its prominent planetarium dome and Art Deco façade, which is adorned with bronze zodiac sculptures, have a traditional appeal. Nestled on an man-made island and surrounded by water on three sides, this planetarium boasts some of the most beautiful views imaginable.
  • Chicago Harbor
    Chicago Harbor is the name given to the collection of piers, harbours, rivers, and lakes that skirt the city's lakefront. You'll be able to enjoy all of the panoramic vistas and boat arrivals and departures while you're here. Sun-seekers can spend the day at North Avenue Beach in Lincoln Park on Lake Michigan, which is known for its spectacular sunrises. The Garden of the Phoenix is a lovely park with a beautiful garden that will leave you feeling rejuvenated and refreshed. There's sure to be something for you at Chicago Harbor, no matter what your passions are.