Apartment holiday rentals in Downtown Chicago

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

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.

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 stay in lively Wicker Park neighborhood!

Centrally located in Wicker Park, Chicago, our property is steps from public transportation and a 15-minute drive to downtown. Ideal for couples, small families and groups, solo adventurers, or business travelers exploring the vibrant city. Please note: our main street location near a hospital may have some unavoidable city noises. Our unit can house 3-5 guests, please review the sleeping arrangements prior to booking. Travel RN friendly, rate negotiable, PM us for info!

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.

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!

Modern Luxury In Old Town - Sleeps 4

Stay in one of the best neighborhoods in Chicago - Old Town! Recently renovated spacious top floor condo with all modern amenities, in a classic 19th century Chicago home in one of the best parts of the city with access to dining, bars, entertainment and more. Ideal for traveling families and friends, and plenty of Chicago culture nearby, from nearly every era. A neighborhood bar with Frank Sinatra's favorite ribs! Michelin-starred restaurants!

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.

Two Bedroom w Porch in Wicker Park

Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

Wrigleyville Inn. Historic Greystone, Free Parking

Have fun with the whole family at this stylish place. Completely rehabbed 3 bedroom 2 bathroom high-end 2nd-floor condo in a historic greystone building, 5 minutes walk to Wrigley Field. And only 2 minutes walk to Clark or Halsted Streets. New open back porch for your enjoyment. Free parking included. Old Grey Lady being reborn. Total gut rehab of classic Chicago 3 flat.