Family-friendly holiday rentals in Downtown Chicago

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

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

Betty BnB

Free admission to The World's Smallest Betty White Museum! Oh, and a comfortable king-sized bed in a newly updated studio apartment. Centrally located in Oak Park, close to cafes and transit. Quiet, friendly neighborhood with ample street parking and a pub across the street. This is a basement unit with a kitchenette (NO STOVE/OVEN), cozy TV room, desk nook, and full bathroom. The bed is king-sized and has a firm mattress. The floors slope and there's no thermostat, but it's cute + welcoming

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

*Entire City Apartment 1 block to Train Park Free

Perfectly private - large & comfortable with full kitchen. FREE & EASY street parking One block to (Green Line) train stop to United Center - Concerts, Bulls & Blackhawk games. Two stops to trendy West Loop Randolph bars, restaurants and shops. 10 minute ride downtown Chicago. Kitchen has cooking utensils & coffee, cream, sugar, spices. Shampoo/conditioner/towels/linens are provided. Free wifi. PLEASE NOTE No visitors No smokers no exceptions and agree per message to confirm reservation

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)

Unwind in Style Steps from the Magnificent Mile

Ideally located just half a block from Michigan Avenue, this apartment boasts high ceilings, beautiful wood floors, with thoughtfully appointed rooms for your comfort. You will have everything you need to enjoy your stay in style! PLEASE NOTE: 4th floor walk-up (NO ELEVATOR). There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard leading up to the apartment but never in the apartment.

Spectacular 2BR Penthouse in the Loop | Roof Deck

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Downtown Mich Ave #10 | 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 Double 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!

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Spacious 1-bedroom South Loop Loft I Sleep 5

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!