Holiday rentals with lake access in South Loop

Stylish Corner 2 Bedroom in the Heart of Chicago |

[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Summer/Fall 2026. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. This stylish corner apartment is in a perfect location with fabulous city views in multiple directions. It's a bright and spacious two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

Lincoln Pk-parking-wifi-King bd-crib-kid friendly

This wonderful 2 bedroom garden apartment in superhot Lincoln Park on a block where homes sell for 4 million to 12.5 million dollars. Walk score 97 The apartment was totally renovated adding new furniture, Flatscreen TVs in both bedrooms and Livingroom, a fully stocked kitchen, superfast wifi (150 Mbps) dedicated parking space, rooftop deck, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop is 2.5 blocks from the apartment. Go to the Cubs game/downtown.

Millennium park 10 min Free P-Spot&Balcony Sleep 8

FREE & SECURE ONE IN-DOOR PARKING SPOT!!! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences. Bring the whole family to this great place with lots of room for fun.

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Lakeview Charmer -with parking!

Walk to Wrigley 4 blocks away: 15 min walk; 3 minute drive. Walk to The Vic (around the corner), the lake, several theaters, many restaurants, RedLine el (1 block) takes you north to Evanston, south to Loop, to Sox. Park your car behind the building. A Garden 2 BR (one semi-private; see pics) with 2 queen beds. With rollaway and couch, could accommodate up to 6. We also have a fold up crib. FYI: NO Smoking inside or on the patio. No animals. See pic on patio: el is a few doors west.

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Spacious Two Story Luxurious Home w/Outdoor Deck!

Our home is in a quiet neighborhood, on a corner with abundant space and natural light. There are two spacious levels with two bedrooms upstairs and one downstairs. The large outdoor brand new deck was designed for barbecuing, star-gazing or just relaxing. Beautifully polished wood floors with a modern kitchen make this home ideal. A claw foot soaking tub is perfect for the end of a day and truly ensures a relaxing stay and a deep, refreshing sleep. Free parking!

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

MICH AVE #5| Downtown Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of Chicago ✅ Central Location ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Shared Rooftop Deck w Grills ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

Secluded 2BR APT in Chinatown by McCormick/DWTN

Located in the heart of Chinatown and close to McCormick Place, with easy access to public transportation into the city. Chinatown is the largest Asian neighborhood in the city with food choices such as Chinese Cuisine, Dim Sum, Asian Fusion, and Szechwan cooking . You don't want to miss the bubble tea, Thai ice cream, and crepes. Please note that our photos are not professionally captured in order to show the true view of our unit.

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

This generously sized, quiet apartment, located in the highly sought-after Lincoln Park neighborhood, offers convenient access to acclaimed restaurants and boutiques, all within a five-minute walk. Its private entrance and proximity—less than four blocks—to both the Red and Brown Line "L" stations ensure effortless access to Chicago's attractions, most within a two- to five-stop train ride. Zoned parking permits are provided.