Discover the Best Vacation Rentals in Chicago, Illinois

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.

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.

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.

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.

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.

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.

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.

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.