Holiday rentals with a fire pit in Chicago

Sunny 1 bedroom apartment 1 block from restaurants

This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

Enchanted Garden Treehouse (Amenity*)

Spring is here, the flowers out, the treehouse warm and cozy, and the hot tub ready! Relax on cool evenings in our luxurious, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall cuts thru snow into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits, foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

Wicker Park Walk-Up Condo

Enjoy the best of what Chicago has to offer. Located in the West Town/Wicker Park Neighborhood, steps away from the exciting Division St. and Milwaukee Ave. lined with great neighborhood bars, restaurants, boutiques, etc. Centrally located steps from public transit (The "L" Train/Bus), the expressway, Goose Island, Lincoln Park, & More. Experience one of Chicago's best and most interesting neighborhoods! This apartment is fully furnished with modern touches, a private rear deck & front patio.

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets Allowed! Bathroom/Shower updated Feb 2025!

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Steps away from Wrigley Field!!

The Wrigley Home is a newly renovated 2-bedroom with spacious living room & dining room. Ideal location for groups & families as this family-friendly neighborhood is walking distance to train stops (Addison- Red Line & Southport- Brown Line), retail shops, bars, restaurants, parks, and more! You will feel like home with a large sofa, fireplace, dining room table, brand new kitchen appliances, the amenities of home, pack and play, high chair, stroller, toys, backyard for grilling, etc.

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. The property has a parking slab in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

ALOHA Tropical Penthouse in Wicker Park Sleeps 14

Follow @bangtel for perks and deals! Look no further for your vibrant city escape! Welcome to your tropical penthouse paradise, ALOHA — a 2,000 sq ft oasis in the ❤️ of Wicker Park. This modern, design-forward retreat blends Hawaiian vibes with bold color, playful energy, and luxurious comfort. Just steps away, discover Wicker Park’s best restaurants, boutiques, nightlife, and parks — the ultimate blend of urban excitement and laid-back luxury.

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Executive Apartment on Lake Michigan with parking

Stay in a furnished 2nd-floor apartment in a walk-in building with its own beach on Lake Michigan. Watch the waves from your living room or sit out on the terrace. -Free Wifi, -Onsite Parking with EV charging station -Steps away from parks, minutes away from universities, shopping, and restaurants -Less than 25 min drive to Wrigley Field, Downtown Chicago, Soldier Field, and museums.