Holiday rentals with a hot tub in Northwest Side

LakeHome Cozy Retreat! HotTub •FirePit•Bar•Fishing

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Andersonville Luxury Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

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!

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

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.

Tea Studio in Wicker Park Spring Factory

There's no other place like it in Chicago. A converted 1900's warehouse in the heart of Wicker Park - Once a Prohibition-era distillery, then a spring factory, and finally reimagined as a one-of-a-kind designer loft. Features soaring 14-foot timber ceilings, exposed brick, and a level of finish that earned a national kitchen award and a feature in TimeOut's "Best in Chicago". The kitchen is massive. The bathrooms are luxurious. Plus, Chicago's best neighborhood is right outside the door.

Entire house in Lakeview with yard and garage

Enjoy the luxury and privacy of a house all to yourself in Chicago's trendiest neighborhood. Very well maintained and furnished since this serves as my primary residence that I make available on Airbnb when I’m out of town. Around the corner there is a 7-Eleven and within a 10 minute walk you’ll find Target, Starbucks, Gym, Theaters, Restaurants, Bars, and much more. You can also easily walk to Wrigleyville, Boystown, or the train station which can take you downtown in under 20 minutes.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Modern Lux 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

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.