Vacation rentals in Jackson Park, Chicago

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Top-rated vacation rentals in Jackson Park, Chicago

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Top guest favorite

Guesthouse in Hyde Park

5 out of 5 average rating, 73 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 favorite

Vacation home in South Shore

4.93 out of 5 average rating, 75 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 Chicago

4.75 out of 5 average rating, 32 reviews

VlP STUDlO - 3rd FLr

Welcome to our 3rd FLOOR VIP STUDIO!!! Located on the 3rd FLOOR of our charming older building. Designed to provide you the optimal comfort and relaxation after your long day. We realize, we’re not a hotel, ergo we may not be a good fit for all; HOWEVER; :) as you decide to try us out, you will not be disappointed you did!! We’re always available to you, our aim; to leave you happier and more refreshed than when you came. AND OF COURSE OUR REPEAT GUESTS GET AN EXTRA 8% OFF WHEN THEY RETURN!

Guest favorite

Condo in Woodlawn

4.95 out of 5 average rating, 43 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!

Superhost

Townhouse in Woodlawn

4.92 out of 5 average rating, 50 reviews

*Hyde Park *2 Masters *2 Living Rooms *Courtyard

Welcome to our newly renovated retreat, The Urban Oasis in Hyde Park. Embrace the artful decor throughout the spacious house only a 10 minute walk to the nearest beach. Rent a bike for a scenic ride to nearby attractions like University of Chicago, Obama Library, Museums, the Natural Walkway Nature Park and the lake. Conveniently located near Hyde Park central to downtown Chicago, this is the perfect stay for families and small groups as you explore everything Chicago has to offer.

Guest favorite

Apartment in Hyde Park

4.93 out of 5 average rating, 115 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. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

Superhost

Apartment in South Shore

4.73 out of 5 average rating, 33 reviews

South Shore Oasis

Discover South Shore's charm in this renovated 1-bed basement apt within the owner's home, perfect for UChicago visitors—parents, graduates, and professionals. Though outside Hyde Park, it's just a 5-min walk to transit, offering quick access to campus and downtown. Enjoy the lakefront, bike trail, and beach nearby. Separate entrance ensures privacy, with the owner on-site for local tips. Experience tranquility with easy access to excitement. Book now for memorable stays!

Apartment in South Shore

5 out of 5 average rating, 3 reviews

Zen's Retreat ~ Quiet, Beach, Golf, 15 min DT

Discover this renovated two-bed, one bath in a historic Chicago bungalow nestled in the South Shore neighborhood. Bathed in natural light, these generously sized bedrooms and a shared bathroom boast modern finishes. Well-equipped & bright kitchen. Spacious living & dining rooms with beautiful decor. Refined & lush landscaping offering front, side, and backyard space with ample sun and shade areas. Nearby access to bus/train, beaches and free street parking is available.

Guest favorite

Guest suite in Hyde Park

4.93 out of 5 average rating, 46 reviews

Classic Den @ U Chicago

Our homey space includes full bath, kitchenette, living area and super comfy Queen bed. Direct access to unit from the exterior rear door makes coming and going easy. Located on University Ave. just a minutes walk to U. Chicago campus, easy access to public transportation taking you downtown in just over half an hour. *Note*This is in the basement of our home. Interior stair door locks from basement side to ensure guest privacy. You will hear us upstairs at times.

Condo in South Shore

5 out of 5 average rating, 4 reviews

Harmony near the lake Modern 3 bed 2 bath

The entire family can enjoy this spacious, modern layout with lots of room for fun. Near the Jackson Park 18 hole golf course, the Obama Center, University of Chicago and the Hyde Park neighborhood. Plus you're near Lake Shore Drive where you'll have great access to other Chicago attractions. The kitchen open and inviting great for entertaining. 2 large and 1 medium bedroom means plenty of room for everyone. This is a great home base for experiencing Chicago!

Apartment in Hyde Park

4.67 out of 5 average rating, 3 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 favorite

Private room in Woodlawn

4.92 out of 5 average rating, 156 reviews

Private BR;Parking by UofC/HydePark

This comfortable condo is a stones throw away from Hyde Park and University of Chicago. The space is great for visiting parents, researchers or professors. Your room features wifi, and a 32" TV. Access to the"L", Uber, close to lake, 20 minutes from downtown (depending on traffic). Room can accommodate 3 (4 in a pinch)