Apartment holiday rentals in Downtown Chicago

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

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.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

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!

Alluring Condo w/ Pri. Prkng Cls to Transit &Beach

Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with our fully equipped kitchen, enjoy the 65 inch Roku TV, and gather around the very large island.

The Penthouse Gallery at OHC

Welcome to Open House Contemporary, Chicago's best Airbnb! Featured in Architectural Digest (Aug. 2018) and as one of Bobby Berk's (Queer Eye's designer extraordinaire) top 10 AirBnbs in CN Traveler (Sept. 2018). Come live alongside Open House Contemporary’s latest exhibition from some of America's finest emerging artists. Enjoy lots of natural light from this Penthouse condo through walls of windows or slide open the balcony doors for a relaxed evening at home.

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of Chicago ✅ Central Location ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Shared Rooftop Deck w Grills ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of the Park & Lake ✅ Central Location ✅ Parking garage attached to building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Rooftop Deck ✅ 1 block from Red, Orange, Green "L" subway ✅ Close proximity to Park, Soldier Field, Museums

Chicago Oasis | Spa Bath, Patio & Fireplace

Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Dwtn 10 Min, Free P, PingPong, Sleeps 10

- Spacious, modern 2BR/2BA with free indoor parking, steps from the United Center - Game room with a Ping-Pong table for family-friendly fun after a day of sightseeing - Chef’s kitchen with high-end appliances and a rice cooker for convenience - Relaxing master suite with a walk-in closet, en-suite bathroom, and heated floors - Book now for a comfortable stay with easy access to major Chicago attractions