Holiday rentals in South Loop

The Aerial Oasis

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 1 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Sonder South Wabash | One-Bedroom Apartment

Welcome to South Wabash — your modern South Loop sanctuary. Where each sophisticated space includes a fully equipped kitchen, in-suite laundry, and stunning Chicago views. Colorful art pieces complement the industrial exposed concrete ceilings. And floor-to-ceiling windows burst with natural night. There’s always something to do in the Windy City. Whether you like jazz, opera, or dive bar karaoke, the South Loop has entertainment for everyone. At South Wabash, experience the best of the city.

Kasa | 1BD, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

ChicagoTreasure, Art Gallery w/Parking

Welcome! This large sunny bedroom with individually controlled air conditioning is located in an art gallery in Chicago's vibrant artist and historic neighborhood named “Pilsen.” It is situated on the famous 18th Street near to Harrison Park and The National Museum of Mexican Art. The Pink elevated train line a block away will bring you to the Chicago downtown Loop in 15 minutes. There are many fun and hip restaurants, cafes, musical venues, parks, and cultural events available nearby.

Studio with View of Skyline in Heart of Pilsen

Explore Pilsen and the beautiful City of Chicago in this unique Loft Style Studio apartment with a view of the Willis Tower and in the Heat of Pilsen. Apartment features a Roku TV with Wifi, private entrance, open layout, closet, bathtub with handheld shower head. 1 queen bed and a sofa bed couch, no kitchen but does have a fridge. Unit is on the 4th floor, no elevator. No Private Parking, just street parking . Located near major transportation, Divvy Bike Station across the street.

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Sentral Studio Apt in South Loop Chicago

Indoor/Outdoor Resort-Style Pool • Grilling Station • Four-Story Indoor Garden • Fitness Center • Demonstration Kitchen • Pet Friendly w/ Amenities • Co-Working Space w/ High-Speed WiFi • Across from Grant Park • Steps to South Loop Dining & Nightlife • Breathtaking Views of Lake Michigan & the City Skyline Sentral Michigan Ave offers upscale comfort in the heart of Chicago’s South Loop, blending premium amenities with unmatched access to parks, culture, and entertainment.

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Egyptian Room - Free Parking, 1 block to CTA

Comfortable lower level bedroom with a pillow top king bed, granite topped desk, and smart tv makes this room a super cozy retreat, You will have full access to the kitchen cooking and free Keurig coffee. You have a private mini fridge in your room for food storage. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms. Easy unmetered street parking is readily available for those coming by car.

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Loft Style Private Apt 2 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.