Holiday rentals with breakfast in The Loop

Historic mini mansion!

The whole group will be comfortable in this spacious and unique space. With generously sized rooms and two and a half bathrooms, there’s plenty of space for families or groups. Each room tells a story, with original woodwork that whispers the charm of a bygone era. Explore the original craftsmanship of Chicago reflected in our stunning staircase, the proud centerpiece of the home, inviting you to ascend to the second and third floors where comfort meets character. Close to the new Obama Center!

Family · Location · Outdoor spaces

Huge, sunny 3 Bed/2 bth Apt, free parking, near NU

This large, sunny, second-floor, walk-up apartment is centrally located, about a mile from Northwestern University and close to parks, trails, and Lake Michigan. Featuring 1600 sq feet of hardwood floors, bright windows, and brand-new stainless-steel appliances, this space blends charm and convenience. Enjoy the comfort of central air and heat, 3 bedrooms, 2 full baths and in-unit washer/dryer. The neighborhood is peaceful and quiet, yet walkable to grocery stores, restaurants, and coffee shops.

Location · Family · Nearby

Cheerful Remodel Prime Location

Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.

Location · Value · Hospitality

Gallery Loft of Oak Park #1 Top Host in IL

Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

Value · Family · Decor

Brand New Luxury space + roof deck!

Your family will be close to everything when you stay at this peaceful and centrally-located place. Our space is centrally located on the north side of Chicago, 11mins from O’hare international airport (8 miles) and 13mins to Downtown Chicago (10 miles). In the heart of Chicago finest transit hub (Jefferson Park Transit Center). You can get on the Blue line trains from the airport or to downtown Chicago, buses going to different part of the city. You don’t have to deal with parking Downtown.

Value · Family · Comfort

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!

Location · Value · Condition

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

Value · Family · Beach

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Location · Value · Quiet

A Vintage Pink House in the Heart of Chicago

Located in a quirky, Victorian era, pink house on a residential street in the East Village neighborhood, this unit is a charming piece of Old Chicago. This 2nd story, apartment features an eat in kitchen, a double and a single bedroom, and a front room that oozes Chicago history. Perfect for a quick weekend getaway or an extended stay. A Walk Score of 97 means you won't need a car to experience the city. Easy access to Division Blue Line, nightlife, shopping & adventure.

Value · Family · Breakfast

Luxurious Bronzeville Apartment with RoofTop

Your cozy getaway awaits in Chicago at this beautiful apartment. With three bedrooms featuring two queen beds and a futon, there’s plenty of space for guests to relax comfortably. The apartment includes two bathrooms, each thoughtfully equipped to make your stay easy and convenient. Whether you’re unwinding after a day of exploring or preparing for a night out, this charming spot offers a welcoming atmosphere. Enjoy all that Chicago has to offer when you stay at our place.

Location · Family · Parking

Bronzeville Tribe Palace Loft

Central Prime Location: - Downtown (7 min) - McCormick Place (5 min) - Soldier Field (5 min) - Rate Field (5 min) - Chicago Lakefront (5 min) - Obama Library (5mins) Amenities: - 3 queen beds - 2 full baths - 4 Smart TVs - 3 workspaces - High-speed Wi-Fi - Fully equipped kitchen + new appliances - Complimentary coffee, tea, oatmeal + fruit - Spa-quality toiletries - Private rear porch - Shared backyard lounge + grill - Self check-in - Free street parking

Family · Location · Decor

West Loop 2BR : Skyline Views + Prime Location

Your perfect Chicago base with easy access to everything will make for an unforgettable adventure. Enjoy a private balcony and exceptional amenities in the building. You will want to come back and stay again! Join our growing list of 5-star reviews! All guests this year have given a perfect score for our cleanliness, accuracy & communication.

Value · Family · Barbecue