Apartment holiday rentals in Downtown Chicago

2 bedroom• 3 beds • 1 bath Apartment in Berwyn

Enjoy a stylish and elegant experience at this centrally-located private apartment On famous Route 66. Sunny, clutter free very spacious 2nd floor. Apt. Can sleep upto 6 ppl. Inflatable bed added for extra sleep option. Prepped for photo sessions of your own. •Restaurants, Auto repair shops and Walgreens are walking distance and much more. •Metra is a 10-15 minute walk. •DT Chicago 18 min •Brookfield Zoo 15 min Away •Midway Airport 15 min •O’Hare Airport 30 min •Mall 10 min •Loyola Hospital

1 Bedroom Cute & Cozy Bi Level Loft Style Apt

Cozy & Cute 1 bedroom bi level loft style apartment. Entire space to yourself! Full size Washer & Dryer, parking on premises, close to public transportation. Everything in area for all your needs including Starbucks, restaurants, smoke shops, etc. 15 mins from downtown Chicago, 15 mins from Oak Brook & Yorktown Shopping Center. Very convenient, easy to access. ***PLEASE NOTE pictures of unit where updated as of 2/14/26 there is new furniture and freshly painted so please ignore past reviews

Galactic Getaway | 2BR Near Chicago & Airport

Step into this modern and stylish apartment 20 minutes from Downtown and Midway Airport, with a galaxy nebula projector that turns the living room into an experience kids (and adults) love. This 2 BD, 1 BA in Berwyn sleeps up to 5 guests and is set up for families, friends, or anyone who wants a comfortable home base without downtown prices. Everything you need for a short trip or an extended stay. ✔ 70" 4K TV + TVs in Bedrooms ✔ Two Queen Beds and Full-size Pull-out Sofa Bed ✔ Full Kitchen

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Treetop Oasis With Parking Walk To Town & Train

Take a deep breath and relax in this airy and bright top floor apartment. Treetops surround the newly renovated and spacious home in a premier Oak Park location. 20 min. to downtown Chicago. Only 1/2 block to the FLW Home & Studio. Walk to dining & train. 2 bedrooms & 1 bath w/tub & shower. Open living/dining/kitchen/sunroom. Wow kitchen w/huge island. Primary w/king bed + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Shared fenced yard. Driveway parking.

First floor of Historic Oak Park Villa, Grge:2Cars

Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Frank Lloyd Wright homes, 30 min from the Loop, MDW and ORD, makes this location an ideal platform for the cultural explorer. Experience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends. Gig-speed internet supports sophisticated professional and gaming applications.

Restful Retreat Perfectly Located by Train+Shops

This bright and sunny apartment will be your perfect home base for exploring Oak Park or Chicago. Come home to a quiet and restful retreat with high end mattresses, multiple coffee options, and well-stocked bookcases. We are steps from the train to the city and from the best Oak Park has to offer, from shops to restaurants to world famous architecture. The unit is in a brick building, set back on a long lawn, making for a peaceful stay with all the amenities of the city!

Bright Boho Haven free parking

Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!

2 Bed Apartment | Convenient Access to Downtown

Enjoy your stay in Forest Park in this modern, newly remodeled two-bedroom apartment on the first level of a three-unit building! It is conveniently located just off the highway, depending on traffic, and only a 20-minute drive to downtown Chicago. O’Hare and Midway Airports are about 30 minutes away. The apartment comfortably accommodates up to 4 people, with two private bedrooms featuring queen beds and a pull-out sofa in the living room.

Modern|Aesthetic|2BR|Evanston|Near Beach

1st floor with 1 flight of stairs. Older building with radiant heat managed by building. Welcome to this beautifully remodeled 2 bedroom, 1 bathroom unit in the highly sought-after neighborhood of Evanston! With an abundance of natural light flooding in, this unit boasts a warm and inviting atmosphere that will make you feel right at home. Our apartment is located right next to the beach and a very nice path along the lake.

Train ride to Chicago, welcome home

The garden apartment is small but mighty! It features a full kitchen and bathroom and a laundry facility onsite. You can walk 10 minutes to the blue line to Chicago. Large yard with an outdoor cabana and seating areas. Close to park and grocery store. Please make sure you are accurate on your guest count, do not put one guest when there will be 3 (for example). Welcome to my slice of heaven in Forest Park!

Bright & Spacious Victorian-FREE PKG walk to train

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago. We kindly ask that you read our full listing description and our house rules prior to booking.