Luxury Vacation Rentals for Large Groups in Chicago

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 2 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in Chicago

Wander Chicago Modern

Next avail.

Dec 7 - Dec 9

516

Welcome to your large group retreat in Chicago

Bring everyone together in Chicago with room to spare. Wander offers luxury large-group vacation rentals in Chicago that pair five-star polish with the comfort of a private home. Think expansive lounges for movie nights, long dining tables for shared meals, and multiple ensuite bedrooms so every guest has a true retreat.

Every Wander includes ultra fast WiFi, hotel-grade linens, pristine cleaning, and 24/7 concierge. Chef-ready kitchens simplify catering or cooking, while quiet work nooks keep productivity effortless. With thoughtful floor plans and smart home features, our Chicago collection makes hosting reunions, milestone celebrations, and team offsites feel effortless from arrival to checkout.

Popular large group vacation rentals in Chicago

Chicago, Illinois

Wander Chicago Modern

Available soon in Chicago

Wander Chicago Modern

Next avail.

Dec 26 - Dec 28

516

Highlights in Chicago

Discover iconic architecture, world-class museums, and vibrant parks, offering endless entertainment and dining options for groups of any size.

Millennium Park

Navy Pier

Chicago Riverwalk

Willis Tower Skydeck

Art Institute of Chicago

Field Museum

Wrigley Field

Lincoln Park Zoo

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Chicago

Wander Chicago Modern

Most popular amenities for large group vacation rentals in Chicago

Exercise Equipment (1)

Outdoor Dining Area (2)

Foosball Table (1)

Fire Pit (1)

Other popular amenities & vacation types in Chicago

Family vacation rentals in Chicago

Hot tub vacation rentals in Chicago

Discover more large groups activities in Chicago

Chicago rewards curiosity at every turn. Lake Michigan sets a dazzling backdrop for skyline views, while world-class arts, architecture, and sports deliver a cultural calendar that rarely pauses. Explore the Chicago Riverwalk, take in marquee performances in the Theater District, or sample a dining scene that ranges from James Beard winners to beloved neighborhood classics.

Seasons add their own rhythm. Summer brings lakeside days and open-air festivals, autumn pairs crisp air with gallery openings, and winter lights up with markets and ice skating. With two major airports and easy transit, the city is as accessible as it is vibrant. This is why Wander’s luxury vacation rentals in Chicago are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Chicago

Why should I book a Wander in Chicago over other large group vacation rentals?

Wander offers a level of consistency and quality you won’t find with most large group vacation rentals.

Every home in Chicago delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular large group vacation rentals in Chicago?

Some of our most popular large group vacation rentals in Chicago include Wander Chicago Modern, Wander Chicago Sky, and Wander Chicago Sky. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different large group vacation rentals does Wander have available in Chicago?

Wander offers 2 large group vacation rentals in Chicago, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s large group vacation rentals in Chicago?

You can check-in to Wander large group vacation rentals in Chicago after 4.00pm and check-out before 10.00am.

Do Wander’s large group vacation rentals in Chicago have WiFi access?

Yes. Every Wander home in Chicago has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.