Discover the Best Vacation Rentals in Chicago, Illinois

The Cloud Gate sculpture, also known as the Bean, is one of Chicago's must-see monuments
The Cloud Gate sculpture, also known as the Bean, is one of Chicago's must-see monuments | © JLImages / Alamy Stock Photo
Photo of Nick Dauk
17 August 2021

Skyscrapers dot the shore of Lake Michigan in the famous Windy City. Stroll through Millennium Park, browse multimillion-dollar artwork at the Art Institute of Chicago or admire the view from the top of the 360 Chicago Tower. Chicago is pedestrian- and cyclist-friendly – and with a fantastic subway system, you can effortlessly venture into every corner of the city. Staying at a Chicago vacation rental is the next best thing to living here, and these self-catering stays will make you feel right at home – all bookable with Culture Trip.

Sonder – The Bel

A contemporary vacation apartment wit full kitchen and luxurious living area at Sonder – The Bel.
Courtesy of Sonder – The Bel / Expedia

Deep-dish pizza and the Chicago Cubs: two classic Chicago staples that are only footsteps from these Belmont Avenue suites. These deluxe Chicago vacation suites, featuring kitchens and a rooftop terrace, are within walking distance of Wrigley Field and Giordano’s deep-dish pizza parlor. We can’t guarantee that the Cubbies will win, but we can promise you that you’ll be filling your apartment’s refrigerator with enough slices of deep-dish to feed you for the rest of your trip – and that’s just if you order one pie.

Sonder at 943 Crosby

A contemporary seating area in a vacation apartment at Sonder at 943 Crosby.
Courtesy of Sonder at 943 Crosby / Expedia

Leave the lake by the shore and spend your Windy City getaway near the Chicago River at these one- and two-bedroom vacation apartments in Chicago. A kitchen, wifi, laundry facilities and all of the other creature comforts make this apartment perfect for remote working or easy-going holidays. Hilarity ensues at Second City comedy club, just a five-minute drive away, but we recommend hopping the Purple or Brown Lines so you can spend the night laughing your way around town.

Sonder – Greektown Suites

A copper-framed king size bed in a vacation apartment rental at Sonder — Greektown Suites.
Courtesy of Sonder — Greektown Suites / Expedia

Check a visit to the Willis Tower off of your to-do list with ease during your stay at these Greektown guestrooms. Within 15 minutes, you can reach the iconic skyscraper, leaving your group ample time to sleep in and laze about your premier three-bedroom suite. You can spot some of the best gyros and tzatziki from the rooftop terrace – it’ll taste delicious if you order in and munch on it on your private terrace.

Kasa Chicago South Loop Apartments

A contemporary vacation rental overlooking the city from Kasa Chicago.
Courtesy of Kasa Chicago / Expedia

Get a breath of fresh air in Chi-town’s South Loop at these laid-back Chicago apartment rentals. Whether a studio will suffice or if you need the extra legroom in the superior apartment, we have a feeling you’ll be spending most of your time on your private balcony or on the rooftop terrace. Loving the Chicago breeze? Keep the kitchen clean and the TV off – the stunning lakefront parks like Buckingham Fountain and Grant Park are a half-mile walk from your apartment.

LEVEL Chicago – Old Town

The rooftop pool area at LEVEL Chicago, Old Town.
Courtesy of LEVEL Chicago – Old Town / Expedia
Whether you want to hit the beach, see the Bean, or try the best pizza parlor in Old Town – hello, Happy Camper Pizzeria – LEVEL River North’s aparthotel puts you within minutes of it all. The in-room washer and dryer are super convenient for rinsing off your swimsuit after a day spent at Oak Street Beach or in the on-site pool. These deluxe vacation rentals in Chicago, which sleep up to four, are also pet-friendly, while the 7 acres (3ha) of doggy heaven that is Seward Park is only a block away.

Sonder – The Plymouth

A rooftop patio with contemporary seating at Sonder – The Plymouth.
Courtesy of Sonder - The Plymouth /
You’re always in the Loop at Sonder’s the Plymouth apartments. Ranging from singles to three-bedrooms, which sleep as many as eight guests, these vacation homes in Chicago have full kitchens alongside areas to work, relax and dine. A communal fitness center and outdoor terrace are great perks – but the best way to get your body moving is by walking a few blocks east to the Lakefront Trail adjacent to Grant Park. Though there is no parking on site, the Harold Washington Library-State/Van Buren subway station is only a block from your room.

Sonder at South Wabash

A contemporary bedroom with floor-to-ceiling windows at Sonder at South Wabash.
Courtesy of Sonder at South Wabash /
Staying in Sonder at South Wabash apartments offers the creature comforts that you can’t live without – even on vacation. A gym, washer and dryer, full kitchen and infant bed are all included in your stay. Whether you need a two-bedroom that sleeps a family of six or a cosy studio for you and your partner, these apartments are perfectly located less than a 30-minute walk from kid-friendly attractions like the Shedd Aquarium, Grant Park and the Field Museum of Natural History.

Kasa Chicago River North Apartments

A contemporary bedroom in a vacation rental at Kasa Chicago River North.
Courtesy of Kasa Chicago River North Apartments / Expedia
Your shopping spree begins as soon as you roll out of bed in this gorgeous Chicago vacation apartment complex, only three blocks away from the Magnificent Mile. The Whole Foods on site lets you get the most out of the full kitchen – but there’s a Starbucks Reserve Roastery and a Giordano’s around the corner, if you want to fuel your vacay with fresh coffee and humongous deep-dish pizza slices. Apartments range from studios that sleep three to two-bedrooms for six, but all include a comfortable living room with amazing downtown views.

If you’d like to explore the rest of the state, check out the best vacation rentals in Illinois, bookable with Culture Trip.

This is an updated version of an article originally written by Tara Gardner, with additional reporting by Josh Taylor.

These recommendations were updated on August 17, 2021 to keep your travel plans fresh.

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