Vacation rentals with a fire pit near Soldier Field

The Metropolitan Retreat (Fitness Center • Sauna)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Charming retreat w/ fireplace

Experience the soul of Chicago in this unique, tranquil getaway nestled in the heart of historic Pilsen! Immerse yourself in the neighborhood's famous murals and vibrant culture. 🏠 The Space: Spacious & bright with a private bathroom for the main bedroom plus an in-unit washer/dryer. 📍 Pilsen Living: 🛒 5-min walk to Aldi 🌮 Steps to taco trucks & cozy bars 🍕 BYOB pizza nearby 🚶 Transit: 3-min walk to the Pink Line/Bus 🚗 15-min to Downtown/McCormick Place Check out my other listings!

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.

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.

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

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

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!

816 PLZN Penthouse| Rooftop| Indoor Garage Parking

Welcome to your stylish retreat in vibrant PILSEN! This modern apartment offers garage parking, a rooftop with stunning views of Willis Tower, and a cozy firepit for relaxing evenings. Explore the neighborhood's murals, visit local bars like Simones, and enjoy Sunday brunch at Duseks. Catch a concert at Thalia Hall or sing your heart out at karaoke bars nearby. Experience the best of art, food, and entertainment in PILSEN – book your stay now!