Holiday rentals with outdoor seating in Downtown Chicago

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

The Lakefront Lookout (Rooftop Deck • Gym)

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, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city!

Perfect Spot & Spacious 2BR+2BA | Mapletree Suites

Welcome to Mapletree Suites! Our stylish, clean, and contemporary 2 bed+2 bath suites are located in a boutique building in Chicago’s booming West Loop neighborhood. Keyless entry, blazing fast WiFi, bright white linens, in-unit laundry, 10ft ceilings, balconies, Italian cafe, host on-site, plus much more! Steps from Target store, parks/athletic field, CTA, and close to United Center, world-class restaurants, loop/lakefront, Med District, UIC, corporate offices and highway network. Book today!

Huge Downtown Penthouse #4 | Park, Museums +gym

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: ✅ It's Unique! ✅ High loft ceilings ✅ FAST WIFI ✅ Spacious layout ✅ Comfy beds ✅ Central Location ✅ Private Balcony! ✅ Close proximity to Grant Park, Soldier Field, Museums, and more! You are a short walk to Millennium/Grant Park, Skydeck, Shedd Aquarium, Adler Planetarium & many dining + shopping options!

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

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.

Studio flat in the heart of Chicago's Gold Coast

Come stay in our one-bedroom studio apartment with a fully equipped kitchen and bathroom. Take in the perks of our central location with easy access to the Gold Coast beach and public transportation. Gibsons and the Original Pancake House are also a stone’s throw away. The property is the perfect refuge after a long day in the Windy City or sunbathing on the beach. After working hard and playing hard, a comfy bed with high-quality linens ensures you’ll be rested and ready for the next day.

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.

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach

FREE GARAGE PARKING! Garage Clearance 6ft. Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

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!

Fulton Market Loft | Rooftop Fire Pit | Parking

Featured in Condé Nast Traveler and Architectural Digest. Rated top 1% of all Airbnb listings nationwide. Two-level loft in the heart of Fulton Market. Soaring ceilings, floor-to-ceiling windows, gourmet kitchen with exposed brick, 3 bedrooms, 2.5 baths, in-unit laundry, and dedicated parking. Step outside to a private rooftop terrace with fire pit and panoramic skyline views. Steps from MICHELIN-recognized Taquería Chingón and Restaurant Row.

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.