Vacation rentals with a fire pit in North Side

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Private Roofdeck! Location! Parking! Amazing home!

Large Bucktown home with plenty of space for the whole family! Your group will have the best stay in the perfect location to explore all that Chicago has to offer. Steps away from the 606 walking trail and one block from the Blue Line. This home is situated on a beautiful tree lined street with charming bungalows highlighting Bucktown architecture. The home offers 2 floors of living space with a large kitchen, dining room, living room and 3 bedrooms. Custom bath with w/d. Parking included!

Grace House | Cozy, contemporary + convenient 2-BR

Make yourself at home in our newly renovated, spacious and immaculately clean 2-bedroom, 1-bath condo — perfect for your next family, work or friends' trip. Located on a tree-lined street in a family-friendly neighborhood and walkable to shops, restaurants, cafes, bars and more. A stone's throw to Southport Corridor/Wrigleyville/Lakeview, Lincoln Square, Roscoe Village and everything the Northside has to offer. Gigabit internet w/ WiFi and everything you need to live and thrive in Chicago.

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Level 2 EV charger available.

Entire first floor in Lincoln Square!

First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

Your Chicago Retreat

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!

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 are Allowed!

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine. This is a quiet, owner-occupied property best suited for travelers visiting Chicago. It’s not intended for gatherings or local stays.

Northside Chicago Getaway

This home is a classic Chicago bungalow that has been recently updated. There are some special features including whole home audio, a 75" TV with 9.1 Dolby atmosphere surround sound, a 3-person sauna, complete kitchen, fire pit out back and private parking for 2 cars. The Home is located in the Mayfair Park area of Chicago and offers a taste of the City life but also has a little space to breathe. Hope you enjoy it as much as I have over the years!

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."

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!