Apartment holiday rentals in Downtown Chicago

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Top-rated apartment rentals in Downtown Chicago

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Guest favourite

Flat in Logan Square

4.96 out of 5 average rating, 379 reviews

King Bed, Huge Spa Shower, Dining Destination

This home was designed with love! Inspired by our favorite boutique hotels - nestled on a tree-lined street in Logan Square, a locals-only destination for brunch, coffee, craft beer and cocktails. Relax in the massive custom steam shower or catch up on HBO on the 50” WiFi TV. Luxe details throughout -premium espresso, memory foam beds and upgraded linens, fully-equipped kitchen. Both bedrooms have private baths, lots of outlets and huge walk-in closets. Easy parking! Central location- Quick walk to Blue Line Train (DIRECT to ORD) - 10 / 15 min to anywhere- Loop, Wicker Park, Lincoln Park! We have tried to attend to every detail- I love boutique hotels and I wanted our Airbnb to reflect that experience. This is a two-bedroom, two-bath private apartment and the garden level of our historic greystone, a classic Chicago property type. The space was newly renovated for friends and family - a luxurious city getaway surrounded by our favorite restaurants. It is warm and cozy with in-floor heat. Truly easy street parking, a rarity in the city. Five minute walk to train at Logan Square Blue Line (20 min direct connection to O’Hare Airport/ORD) and around the corner from top-rated restaurants-blocks to Fat Rice, Longman & Eagle, and Lula, all Michelin rated. Don’t miss brunch at Jam, pozole at Quiote and tiki drinks at Lost Lake, ranked one of the fifty best bars in the world- all walkable. The master has a king-size memory foam bed, individual reading lights with dimmers, and an ensuite bath with massive walk-in steam / rain shower. Second bedroom has a cozy memory foam double bed, private ensuite bath with new oil-rubbed bronze fixtures and cast iron Kohler tub. Both beds have premium 100% cotton linens, black out shades, nightstands with convenient outlets, and walk-in closets -- plenty of room for luggage. Our brand new kitchen has lots of bells and whistles -a Bosch convection oven, garbage disposal, ice maker, filtered water built into the sink and pantry with starter items for cooking. We offer unlimited Nespresso and a french press with whole bean Intelligentsia, our favorite local coffee. Enjoy a night in with our 50" 4K WiFi TV - HBO, Netflix, Amazon Prime, and Spotify Premium are logged in and ready to go. Private entrance. Lots of extras while preserving the character of a classic Chicago home. You're welcome to enjoy the backyard (we have great neighbors). Trash / recycling through gate behind yard. Shared free laundry. I'll meet you at check-in if possible and make some recommendations. I have lived in Chicago since 2001 and love to share tips about my favorite city in the world. I'm a real estate agent and easy to reach, but otherwise, the home is yours to enjoy! Diner’s paradise! Four blocks to Blue Line- This cozy garden retreat is a half block to the neighborhood’s famous Logan Boulevard, lined with park space and historic mansions. Steps to independent coffee shops, brunch and the city’s best cocktails. Walk to tropical drinks at Lost Lake, Michelin rated gastropub Longman and Eagle, fresh pasta at Daisies and local favorite Lula. You’re also an easy eight minute walk to the Logan Square Blue Line. Easy / free street parking. Logan Square is extremely central. We are a four block walk to Blue Line Train (which connects directly to ORD/O’Hare Airport!) and joins all trains with a 15 minute ride South toward the Loop. The Blue Line runs underground and does not share tracks- it is by far the fastest city train line. This neighborhood is particularly easy for cabs as you are only 2 minutes from the 90/94 Expressway: - 10 minutes to Wicker Park - 10 minutes to Lincoln Park - 8 min to West Loop/Fulton Market -15/20 min to Magnificent Mile/Wrigley This is the garden (ground) level of a two-flat- You will hear occasional footsteps above but residents are respectful and polite- they are two professional women and not early risers! Based on my personal spent time in the unit, this will not impact your experience in a significant way. Although we have honored historic details wherever possible, this is a brand new apartment with great insulation. We offer a white noise machine just in case. Ceilings are over 7 ft and while not soaring, tall guests have been comfortable. The unit has radiant in-floor heating (no cold feet!) controlled in your unit with a traditional thermostat. Because it is an English garden and partially below grade, the temperature is very stable. We have window air conditioners for summer.

Guest favourite

Flat in West Town

4.92 out of 5 average rating, 329 reviews

Bright, Modern Apartment in a Vintage Greystone

Enjoy morning coffee by the sunny bay window in this vintage apartment with classic modern style. The apartment features vintage charm with modern amenities, queen memory foam bed in bedroom and queen sofa bed in living room. Parking is available in the back lot for an additional $25 per night. For reservations over three weeks, we require a cleaning every 2 weeks at a cost of $60 per cleaning. Apartment is located on the 3rd floor of a three story building and you will need to climb stairs. This is a large 1100 square foot fully renovated 1 bedroom apartment on the third floor of a beautiful vintage Chicago Grey Stone. Located directly on Chicago Ave. The space was thoughtfully designed by the design firm of Inside Home with the modern traveler in mind. The furnishings are a mix of vintage and new pieces specially curated for the space. The bedroom features a queen memory foam mattress as well as a 42" TV. The kitchen is equipped with cutlery, cooking utensils, coffee maker, espresso machine, pots & pans, baking sheets. Walking Rating of 96! You will have access to the full 1100 square foot apartment as well as a parking spot if needed located directly out back for an additional $20 per night, please notify us at the time of booking if you will require parking and we will add this fee to your reservation. There is also a washer and dryer in the basement if need (please request access) We will be on site at the furniture store located on the ground floor of the building should you need anything during your stay. Ukrainian Village is a historic community known for the contemporary restaurants, bars, and shops along bustling Chicago and Division Streets, but explore the neighborhood further to discover homes and businesses as old as the city itself. You are steps away from the 66 bus, which will take you directly to Navy Pier, rent a bike and explore the city or catch a cab right out side the front door or jump on the blue line "EL" train. This apartment has a walk rating of 96, bike rating of 90 and a transit rating of 72! This apartment is located on the third floor of a three story walk up. There is a additional queen bed in the sofa of the main room and all the additional bed linens are located in the bedroom night stand and closet.

Guest favourite

Flat in Lincoln Park

4.98 out of 5 average rating, 302 reviews

Redesigned Lower Level Studio in Historic Building

The space is very comfortable, quiet and cozy. There are new cabinets, granite counter tops, all new appliances and a washer and dryer. Guests sleep on a king size tempur-pedic mattress or a queen size trundle style pull out sofa. There is hi-speed wi-fi, cable TV (Showtime), 55' flat screen TV and a wood burning fireplace. The bathroom is immaculate and includes a full bathtub with shower. This is a private apartment and you will have access to the entire suite. There is a back and front door with adequate lighting and easy access for guests. My family and I live next door and I will be available at our guests convenience. I am happy to provide any information, recommendations, directions etc.. I am easy to reach and am always available but will not intrude on our guests privacy. This unit is on a beautiful tree lined street in the heart of Old Town, close to St. Michael's Church, Steppenwolf Theater, and the Second City Improv Theater. The location allows for easy access to all of Chicago by either train, bus, or car. The blue and brown line train stations are within walking distance. Street parking is readily available and no permits are necessary. A Chicago Cab or Uber can get you to Milleniumm Park in approx. 15 minutes. Four adults can comfortably stay in this unit. The king size tempur_pedic mattress is the pinnacle of comfort and the queen size trundle style pull out sofa is comparable to sleeping on an actual queen size mattress. The queen size bed could comfortably fit 3 children. There is street parking readily available but I can provide an assigned space behind the building if necessary, for additional cost.

Guest favourite

Flat in Lincoln Park

4.99 out of 5 average rating, 197 reviews

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.

Guest favourite

Flat in West Town

4.98 out of 5 average rating, 224 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Guest favourite

Flat in Avondale

4.97 out of 5 average rating, 120 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Guest favourite

Flat in Humboldt Park

4.98 out of 5 average rating, 109 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Guest favourite

Flat in West Town

4.96 out of 5 average rating, 265 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

Guest favourite

Flat in Roscoe Village

4.95 out of 5 average rating, 242 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Guest favourite

Flat in Uptown

4.96 out of 5 average rating, 268 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Guest favourite

Flat in The Loop

4.9 out of 5 average rating, 113 reviews

Bright 2BR-2BA steps from The Bean & Michigan Ave

Come enjoy this comfy and spacious 2BR-2BA apartment just steps away from Michigan Ave and ‘The Bean’, and within a short walking distance to most of Chicago’s most popular landmarks. Within just two blocks, you will find access to all CTA train lines. With a fully stocked kitchen, smart TVs in all rooms and views to the lake, this is the perfect Airbnb for couples, families and business travelers during their time in the city of Chicago.

Guest favourite

Flat in Little Italy

4.98 out of 5 average rating, 199 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

2 bedroom, 1 bathroom apartment, located just off Taylor Street in the heart Little Italy! Views of the Sears Tower from the front yard. Safe and lively neighborhood, packed with diverse restaurants, cafes, bakeries, parks, etc. all just a short walk from the apartment! Nearby West Loop also packed with trendy shops and amazing dining spots. Flat screen TV in every room, In-unit laundry, patio space, coffee/tea provided. 1pm check out!