Apartment vacation rentals in Andersonville

Adorable Private Edgewater Suite

Cozy exposed brick, garden unit on a quiet street, perfect for relaxing after a night out in the city! Comfy, queen-sized bed, full kitchenette and gated private side entrance so its the perfect spot for your trip to Chicago! We are right by the exciting nightlife of Andersonville and a 10 minute walk to the beach/start of the Lakefront trail. Public Transit is close and easily accessible, the redline "L" can get you downtown in a half-hour train ride. Close to Loyola University, Go Ramblers!

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

Edgewater, private, charming coach house 1 (of 2) Licensed by the City of Chicago 2209375

Our Edgewater coach house is a haven in the city. A ten minute walk to Hollywood Beach, a fifteen minute walk to fun Andersonville and a five minute walk to the 'L' train for direct downtown access, it is near to everything but feels far away from the busy city. Great restaurants are right around the corner, and Wholefoods is three blocks away. Managed 100% for guests, two independent units are superbly comfortable/ pristine. All essentials and more provided. Enjoy the city and relax at once.

Andersonville Bicycle Studio

Enjoy a stylish experience at this centrally-located Andersonville studio. The Bicycle Studio leaves no detail untouched - modern amenities with the charm of exposed brick and timber beams. You are two blocks away from Chicago's popular Andersonville neighborhood - endless dining, shopping and entertainment. Quick access to public transportation and Chicago's lakefront. Quick Note: We are doing a home renovation July 1 - January 2027, so the air bnb will be unavailable during this time.

The Shingle Life • Vintage 1BR Near Wrigley

Think of this place as a small, beautifully odd refuge: a vintage Ravenswood apartment with a sunlit kitchen banquette, a curated mix of Danish furnishings, and just enough whimsy to keep things interesting. All of it on Chicago’s North Side, close to Wrigley Field, Andersonville, and the Brown Line. It’s a space with opinions, but never an attitude. Nice sheets and small design choices that imply the person staying here has great taste. (Reader... that’s you.)

Free street parking - Backyard Oasis

Fun & Funky Andersonville Retreat at Midwest Traveling offers a private chef experience during your stay - reach out for more info! A spacious basement unit that we (the owners) live above. We do have a mini golden doodle on site and if you’d like to meet him just reach out and we can make that happen :) he loves meeting our friendly guests! Andersonville is recognized as one of the coolest neighborhoods worldwide according to Time Outs magazine (Oct 21)

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

Steps to Clark St in the Heart of Andersonville

Enjoy local living on the 1st floor of our classic Chicago 2-flat with modern touches and free street parking. Our location is unbeatable, just a few buildings off of Andersonville's famous Clark Street! We live upstairs, maintain the unit ourselves, and are glad to answer questions. You can easily spend your whole stay in Andersonville or explore our iconic city via quick Uber rides or public transportation.

Urban Garden Retreat, Chic Andersonville Getaway

Fully renovated 2-bedroom, 1-bath garden level apartment just steps away from all the amazing restaurants and shops in the Andersonville neighborhood. 95 Walk Score (Very Walkable) 72 Transit Score (Excellent Transit) 75 Bike Score (Very Bikeable with a Divvy bike rental 0.2 miles away) 0.7 miles to the lake 0.8 miles to Little Vietnam 1.1 miles to Loyola University 2.5 miles to Wrigley Field

Vibrant & Chic Apt On Quiet St in Andersonville

Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...

Beautiful Hollywood-Ridge Suite in Edgewater

Beautiful, complete, and private apartment/suite in a historic Chicago Greystone located in the beautiful and diverse Edgewater neighborhood. Sleeps 1-4 persons (Queen bed in master bedroom and Deluxe Memory-Foam Queen Size Sofa Sleeper in living area). Suite features guest-controlled central air and heat, 2 flat screen TVs, private bath and shower, and full access to all rooms.