Whether you're seeking awesome retreat spots or serene spaces to find peace and tranquility, organize exciting outdoor activities for team building, or enjoy spa treatments, Chicago, Illinois, doesn't disappoint. The city offers more than just those standard hotel ballrooms or a typical restaurant near you.
From boutique hotels with a distinct personality and cozy rooftop bars in prime locations in River North to historic gems and nature-inspired escapes, the Windy City offers tons of venues, many of which are easy to book on Giggster. We have you covered with a diverse selection of affordable, hand-picked retreat venues, ready to bring your vision to life.
The right location makes all the difference to a rejuvenating retreat and a successful event. Lucky for you, some of the best places to relax and escape the daily grind are just a few clicks away on the Giggter app.
Say goodbye to those cookie-cutter venues and hello to Chicago's hidden gems and inspiring spaces like Exterior Offices. The perfect setting is waiting for your group on Giggster.
Maybe you prefer an outdoor space for an intimate family gathering or meeting. An open-air patio in Chicago is bright, airy, and doesn't require a complicated setup.
For overnight retreats for the family or a small group, rent a carriage house or an atmospheric home just ten minutes from O'Hare International Airport. You won't be too far from the action, but you're also close to nature with trails for walking in the woods and a creek that runs through the property.
A trendy, upbeat store by day transforms into a multipurpose event space at night for a chill evening with friends, game nights, and memorable parties.
Play with your favorite person, practice yoga, or simply unwind in a resort-like retreat spot like a luxurious private home in Chicago. The site features a swimming pool, spectacular city views, a wet bar, and your own private balcony for quiet relaxation.
Exceptional Variety & Quality: Refresh your soul, have a great time with friends or your team, let your worries melt away, and find your inner peace among Giggster's 521 top-notch retreat locations in Chicago, Illinois.
Hassle-Free Booking: Finding and booking a convenient healing haven or team-building ground is easier than ever on the Giggster app. Browse our listings, compare your options, view details about each location, and book instantly from the comfort of your own home. You don't need to spend a fortune with rental rates starting at just $20/hour.
24-Hour Free Cancellation Policy: Plans can change, especially when you're coordinating a group. But don't worry because with Giggster, you have a full 24 hours after booking to change your mind and cancel for free, as long as you made your booking at least 48 hours before the event.
Platform Protections: Anything can happen outside of your control, which is why we offer optional liability, damage, and cancellation protection so you can kick back and relax without worrying about the unexpected.
Whether you're a small business in need of a dedicated space for teams to connect, a large corporation trying to increase employee engagement and morale, or a group simply seeking a change of scenery, Chicago has numerous locations to unplug, forget your worries even just for short moments, and find a fresh perspective. But like any decision, it comes with its own fair share of benefits and drawbacks.
Advantages
No matter where your guests or colleagues come from, it's easy to reach Chicago and get around the Windy City, thanks to its excellent train connections and services, as well as two major airports.
There's no shortage of outdoor activities, fun adventures, and entertainment facilities in Chicago, which is great for team-building outings or just letting everyone explore during their free time.
Almost any retreat spot and amenities you can imagine are available in the city. From affordable community centers located in the heart of Chicago to quirky spots and historic spaces, the city has it all.
Disadvantages
Since Chicago is a major city, you'll find its services, food, accommodations, venues, and even activities to be on the pricier side, and many affordable locations fill up quickly if you don't plan early.
Chicago winters are legendary for a reason. If you're planning a retreat or hosting an outdoor gathering between November and March, be prepared for heavy snow, freezing temperatures, and strong winds.
Although the abundance of things to do is a good thing, it can also cause distraction, making it harder to keep your team solely focused on the objectives of your retreat.
Tired of the exact old location for your company retreat or team building? We highlight some of the best traditional and unusual spots in Chicago to choose from that ensure memorable experiences, bringing their own flavor to your adventure.
Private Homes with a Pool – Private and Homey. If your team decides to have an overnight retreat and wants a super relaxed environment to get away from it all, but still within the city, private homes are your answer. Everyone can stay overnight, and it's a bonus if it has a pool (especially in the summer months), a garden, or even a nice backyard, where you can relax and have casual fun after work sessions.
Game Rooms or Entertainment Venues – Fun and Engaging. Find the right balance between spontaneous enjoyment and structured activities in a Chicago game room or entertainment center. Think of arcades, bowling alleys with private rooms, or event spaces with a mix of casual seating and interactive games to unleash your creativity and break down barriers quickly and naturally.
Dedicated Retreat Centers – Focused and Immersive. These venues know how retreats and business events work, so you can rely on them to take care of your visitors. Look for a place that serves as a multi-purpose venue with lodging, catering, meeting rooms, and spacious grounds, so all you need to do is focus on your agenda and achieve your goals.
Lofts – Stylish and Versatile. For something beyond the ordinary, often located in cool Chicago neighborhoods like Fulton Market and the West Loop, industrial lofts are the place to be. Explore options with high ceilings and big windows for that natural light and an airy and spacious feel.
Training Rooms – Productive and Professional. If there are only a few people in your group, training rooms and fitness studios fit the bill. They can be in separate locations, but you'll also find them within hotels, co-working spaces, and convention centers in Chicago.
You want to host an event that your colleagues, family, or friends will enjoy and look forward to, but that's not an easy task. It will require a lot of effort, energy, and money, but it's worth it if it's planned well.
Define Your Purpose – Before you even start looking at venues, checking flight prices, and planning a trip with your travel companions, think about your goal. It makes every other decision much easier and ensures you get the most out of your time (and money!).
Be Realistic with Your Budget – How much can you really spend? Chicago isn't the cheapest city for a retreat, so get a clear idea of your budget early on. If you're upfront about what you can spend, you can filter options faster and avoid falling in love with something totally out of reach.
Pick a Location – Chicago is packed with vibrant neighborhoods, and each has its own offerings and vibe. Select a location that is easily accessible and has the right ambiance, along with activities that everyone will enjoy. Then, schedule a visit to have a feel for the place.
Plan for Activities – What will everyone do there? The activities should go beyond just the work sessions, so mix it up with social events and team building.
You want to save money on your relaxed gathering or meeting in Chicago, but that doesn't mean you have to sacrifice the whole experience. Here are ways to keep your budget in check.
Focus on a quality experience over the number of days.
They say less is more, and this applies to any event as well. And think about it: a jam-packed, two-day retreat where everyone feels inspired, engaged, and energized is probably better than a drawn-out, four-day event where visitors are just counting the minutes until they leave. Cut down on the length of the retreat to save money and focus on a shorter, higher-quality experience.
Does it have to be a centrally located venue?
Downtown (the Loop) and popular areas like River North and Magnificent Mile are super convenient and exciting, but they can come with a hefty price tag. Explore other areas just outside the immediate downtown area that offer fantastic venues at a lower cost.
Can you be flexible with dates and timing?
Summer (June, July, August) is prime time in Chicago. Everyone wants to be there for the festivals, outdoor activities, and beautiful weather, which means prices for everything—hotels, flights, and venues—skyrocket. Consider spring and fall, when services and venues are more affordable.
Looking forward to the days when you can reconnect, unplug from the mundane, rejuvenate, and revitalize? Giggster is here to make the first step easy by helping you find and book the perfect retreat venue in Chicago, Illinois, and beyond.
