Loft vacation rentals in Downtown Chicago

4.92 out of 5 average rating, 255 reviews

Stunning Old Town Penthouse with Private Rooftop

This listing is for the entire building, which is the combination of a penthouse loft (3BR) and the unit directly underneath (2BR), easily connected by private stairs. You will also have a private rooftop deck. This is a beautiful 4,000 sq. ft penthouse loft combined in the heart of downtown Chicago. The building is next to "Magnificent Mile" and steps away from amazing restaurants, comedy clubs (Zannies, Second City), theaters, boutique shopping, public transportation (red line, and 156 bus line), bars and just four blocks from the beach. **Please be aware there are 45 steps to get into the unit (2 flights). This building is truly one of a kind. Built in 1897 and completely renovated in 2016 this unit has exposed brick, 20 foot ceilings and 120 year old barn wood floors capped off with a rooftop deck overlooking Willis (Sears) Tower. 5 bedrooms - 4 with king beds and one with 3 single beds (a bunk bed and a separate single) Also a nook area with a twin bed, built in reclaimed wood; very cute, unique, and comfortable sleeping area! 4 full bathrooms Two full kitchens and two full living rooms. Penthouse master bedroom- Fit for a king. Located on balcony level overlooking living room. Vintage french doors open to balcony. Furnished with a tempurpedic king sized bed and 50 inch TV. Attached to marble bathroom with jacuzzi and all-marble rain forest dual shower head steam shower. Enjoy Kohler faucets and heated floors. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Penthouse second and third bedrooms - Spacious and comfortable, king bed in one, three singles in one. Nicely outfitted with crown molding and large closets. Second Bathroom - Marble floors, classic European style and granite counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Fourth bedroom - Furnished with a cloud like king sized bed, crown molding, exposed brick, and large closet. Remote controlled overhead fan. Connected to a brand new subway tiled bathroom with antiqued brass hardware and a jacuzzi. Enjoy heated floors here as well. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Fifth bedroom - Spacious and comfortable, with cloud like king bed. Crown molding, exposed brick and large closet. Remote controlled overhead fan. Fourth Bathroom - Subway tiled walls with antiqued brass hardware here as well, classic European style marble counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Extra amenities include two push button fireplaces, vintage 1950 Valley pool table, dartboard, surround sound stereo system, PS3 (with movies and games), blu ray, board games and two 60-inch hanging TVs both equipped with HBO, Netflix, Showtime, TiVo, and Amazon each in their own full sized living rooms. Two full laundry rooms in building with irons and ironing boards. Last but not least is the private rooftop deck. This view is absolutely magnificent. Your first walk out onto this large spacious rooftop deck will leave you speechless. It boosts a comfortable couch, grill, and large table all adorned with round draping bulb lights going from corner to corner of the deck, with a full 360 degree view of the Chicago skyline. You will never forget your Chicago visit when you are on the roof deck after the sunsets and the city lights fill up the sky. Spoil yourself in the Windy City. There is nothing else like this in the city. Upon arrival, a welcome packet that will explain to you all about the features of the penthouse and how to maximize your time while staying here. Anything from how to work the jacuzzi to how to operate the electronics is outlined and at your disposal when you walk in the door. We are also pet friendly. While exploring the city we are very centrally located we recommend walking or biking to places like Michigan Ave and the Oak Street beach. A wonderful place to spend an afternoon! There is a parking garage across the street for $26/day located at 1225 N Wells Street. There is also metered street parking. Old Town is an historic area of Chicago right in the middle of the action. It's a perfect base from which to experience the city. Walk or bike to interesting places like Michigan Avenue and the Oak Street Beach. We are very close the the Red Line El train and numerous buses and a divvy bike station. Parking garage across the street. Uber and Lyft are choice methods as well. However, being in the heart of Old Town there is plenty within walking distance.

Top guest favorite

Loft in Forest Park

4.96 out of 5 average rating, 507 reviews

Walk to Oak Park from a Bright Madison Street Loft

Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

4.86 out of 5 average rating, 659 reviews

West Town Traveler's Lodge

Come and stay at my gorgeous 2 bedroom 1 bath condo! It's in a wonderful neighborhood, and in an ideal location for hopping around the city. It's a perfect place to re-energize between big city adventures -> just a 7-10 min walk to the Division St Blue Line Station (3 stops to The Loop). Hardwood floors, granite counter tops, high ceilings, a large back patio, some cool furniture, and exposed brick await in this charming West Town loft. Easy access to both airports via public transit is a plus!

4.9 out of 5 average rating, 121 reviews

Loft in Brookfield

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

4.74 out of 5 average rating, 223 reviews

Downtown Penthouse #5 | Vintage +gym & balcony

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! We are a short walk to Millennium Park, Skydeck, Shedd Aquarium, Adler & many dining + shopping options! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ NEW HVAC Split Units ✅ It's Unique! ✅ High loft ceilings ✅ FAST WIFI ✅ Spacious layout ✅ Comfy beds ✅ Central Location ✅ Big Balcony! ✅ Close proximity to Grant Park, Soldier Field, Museums, and more!

4.77 out of 5 average rating, 569 reviews

Wicker Park Loft - Walk To Everything!

Walk to Bucktown & Wicker Park bars, restaurants & shopping from this large apartment in working artists' building. 10 minute WALK to CTA Blue line TRAIN. FREE STREET PARKING. Premium mattresses and all essentials provided. Resident artists work on the first floor of this historic former telephone repair and switching station. Very laid back vibe. NOTE All guests must be on your reservation for an accurate $total. There is a $30 per night/ per guest charge AFTER 2 Guests (3rd to 5th)

4.88 out of 5 average rating, 395 reviews

Modern, Open, Logan Square Loft w/ Unique Design

Welcome to our open concept studio loft. Located in the heart of Logan Square, we are walking distance to Palmer Square Park, plus some of the cities best coffee shops, restaurants, galleries and summer festivals. This space is airy, naturally lit, and comfortable with a 15' floor to ceiling main atrium, full height windows and custom architectural light screen plus all the amenities to make your stay comfortable. Easy access to public transportation makes getting around the city a breeze

4.9 out of 5 average rating, 412 reviews

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

Top guest favorite

4.95 out of 5 average rating, 531 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

4.85 out of 5 average rating, 105 reviews

Modern, Stylish West Town Loft with Pool Table

Spacious, open, and modern, my two bedroom loft is the perfect spot to welcome you to the Windy City. All the comforts of home are provided to you to ensure a comfortable stay. Downtown is just 10 minutes away, and there's plenty to do within walking distance as well! You'll love exploring the city from this centrally located base, coming back in the evening to shoot some pool and unwind, and resting up to do it all again the next day. Don't miss out on this gem, book today!

4.9 out of 5 average rating, 152 reviews

Entire Loft in Heart of Wicker Park with Parking

Entire floor in one of the coolest neighborhoods of Chicago. You will have access to whatever you desire right here, from it’s amazing abundance restaurants, shopping and cafes to walking the almost three mile walkway of the “606” and it’s rotating installations, observatory and relaxed vibe. At the end of your day you’ll love heading back to your wide open space with its retro inspired furnishings with just the right amount of modern amenities and comfort.