Holiday rentals in Jackson Park, Chicago

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Top-rated holiday rentals in Jackson Park, Chicago

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Guest favourite

Guest house in Hyde Park

4.94 out of 5 average rating, 86 reviews

2 br, 2 bt, UChicago Coachman's Guesthouse

This 2 bedroom, 2 full bath, stand alone UChicago Coachman's House sleeps 5 comfortably. Less than 1/2 mile to the UChicago main quad. Situated on a quiet residential street. Full kitchen to prepare your own meals and dedicated laundry. Easy access from O'Hare or Midway airports. Less than 2 blocks from the Metra train to downtown, Mccormick Place, Soldier Field, Wintrust Arena, Grant Park and Millenium Park. Walk to Trader Joe's, Walgreens, restaurants, lakefront, stores, museums and more.

Guest favourite

Flat in South Side

4.92 out of 5 average rating, 136 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Guest favourite

Apartment in South Shore

4.8 out of 5 average rating, 10 reviews

South Shore Dr Retreat

Enjoy easy access to everything from this perfectly located home base. Walking distance to a 9 hole golf course, beach, and famous Lake Michigan lakefront bike and walking path. Commuters dream with easy access to Chicago bus line and Metra train station. You are close to the following Chicago locations: Lake Michigan lakefront path La Rabida Children’s Hospital 63rd Street Beach Museum of Science and Industry Obama Museum(opening planned in first half of 2026) University of Chicago Hyde Park

Guest favourite

Holiday home in Jackson Park Highlands

4.94 out of 5 average rating, 81 reviews

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. 1 min walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Superhost

Apartment in Woodlawn

4.94 out of 5 average rating, 48 reviews

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Open floorplan, hardwd floors, stainless appliances, 2 Smart TVs in bedrm & living rm, in-unit laundry, and private parking space. Features a cozy reading nook and large outdoor patio. On a quiet treelined street - minutes from Hyde Park and waking distance to Lake Michigan, Jackson Park Golf Course, the 222,000sq ft Regal Mile Film Studios, and upcoming Obama Presidential Library. Your stylish home away from home!

Guest favourite

Flat in Hyde Park

4.93 out of 5 average rating, 125 reviews

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. This is our home, so we are mostly upstairs or nearby if needed. Access is private via back gate just off the parking lot with reserved parking space.

Top guest favourite

Loft in South Side

4.99 out of 5 average rating, 126 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Guest favourite

Flat in Woodlawn

5 out of 5 average rating, 14 reviews

Long Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi

Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its residents' unique way of saying it. :) This vibrantly curated apartment is designed for comfortable extended stays that may make you consider making Chicago home, or at least make sure you feel at home while you're here. You will be welcomed into a well-appointed space with cozy linens, sparkling clean bathrooms and warm touches at every turn.

Guest favourite

Apartment in South Side

5 out of 5 average rating, 24 reviews

Bronzeville Oasis

Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This stylish condo is minutes away from downtown Chicago, the magnificent mile, Navy Pier, Lakeshore Drive, the University of Chicago, and the museum of Science and Industry. You can also enjoy many restaurants in the heart of Hyde Park minutes away on 53rd St. On street parking is available directly in front and beside the building.

Guest favourite

Flat in South Shore

4.71 out of 5 average rating, 7 reviews

Lakeside Chic: An Urban Oasis

Welcome to 7424 S. South Shore Drive Unit 110 Airbnb! Nestled in Chicago's historic South Shore, this cozy retreat is steps from Lake Michigan's shoreline. Explore the nearby South Shore Cultural Center for arts, stroll through Jackson Park, and savor diverse dining options. With easy access to downtown attractions, this location offers the perfect blend of relaxation and urban exploration. Your ideal Chicago getaway starts here!

Superhost

Flat in Hyde Park

4.69 out of 5 average rating, 16 reviews

Sunny Studio by UChicago, Walk to Campus & Museums

Cozy, sunlit studio in the heart of Hyde Park. Just blocks from UChicago! Enjoy a comfy queen bed, fast Wi-Fi, private bath, and a fully stocked kitchen with all the essentials. Located on a quiet, tree-lined street in one of the safest, most walkable areas. Steps from cafes, restaurants, parks, and museums. Easy access to CTA/Metra for trips downtown. Perfect for solo travelers, couples, and visiting academics!

Guest favourite

Apartment in Woodlawn

5 out of 5 average rating, 10 reviews

Luxe Loft vibe | King Suite |4BR 3Ba

Stay in style near Chicago’s best! This luxe 4BR, 3BA loft is perfect for families, professionals, or UChicago guests. Enjoy a king suite with jacuzzi, 3 queen bedrooms with desks, and an open layout with smart TVs, exposed ducts, and dining for 10. Walk to the Obama Presidential Center, Museum of Science & Industry, and lakefront. Adjacent to Hyde Park with quick downtown transit—just 50 min to Indiana Dunes!