Jackson Park Rentals
From $86 per night (USD)VRBO
Modern Coach House 2BR\/1BA\/Den in Hyde Park\/ Kenwood, walk to U of C & Lakefront
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Kenwood Coach House| Rear Coach House Fully Furnished! Near U of C Hospital Hospital Staff/ Clinical Rotations REQUIRE ...
From $86 per night (USD)VRBO
From $348 per night (USD)Expedia
Woodlawn Oasis...10 Minutes to Dining & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Fun times with family and friends at this stylish beautiful home located 10 mins from Hyde Park, (Tiger Woods) Golf Cour ...
From $348 per night (USD)Expedia
From $290 per night (USD)VRBO
Beautiful home with Arcade and Movie Theater for you and your family to enjoy.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This artistic unit is inspired by a collection of unique artwork created by a young Chicago artist. With anime/superhero ...
From $290 per night (USD)VRBO
From $281 per night (USD)Expedia
Spacious 3 bdrm 1.5 bath; Renovated Woodlawn; Incredible Access; UChicago; OPC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This large commodious home is the ultimate place to relax, visit and/or collaborate in our beautiful city. Near the site ...
From $281 per night (USD)Expedia
From $374 per night (USD)VRBO
LakeHouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
Large Parties (3 large beds + 4 Queen Airbeds for additional sleep arrangements). Entertain in style, practice yoga, or ...
From $374 per night (USD)VRBO
From $85 per night (USD)VRBO
Cozy Southshore Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 bedroom 2 bath very cozy spacious in Southshore Chicago. Fully equipped kitchen, Dining room, work space, free WiFi, ...
From $85 per night (USD)VRBO
From $202 per night (USD)VRBO
Spacious two bedroom condo with a cozy feel!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Select this spacious unit as your home away from home. It offers everything you will need as you sit back, breathe, rela ...
From $202 per night (USD)VRBO
From $93 per night (USD)Expedia
Hi-Rise Lakeside Living with Views to Dream by!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Art collecting Superhost's Pied-a-Terre. Spacious, fully furnished, 2 BD, 2 full bath on the top floor of a historic apa ...
From $93 per night (USD)Expedia
From $114 per night (USD)VRBO
Spacious Studio condo in Woodlawn. Steps from Hyde Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This condo is steps from Hyde Park and the University of Chicago. It features floor to ceiling exposed brick walls, high ...
From $114 per night (USD)VRBO
From $828 per night (USD)Expedia
Luxury off the Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
If you want to experience an authentic historic piece of Chicago, walking distance from lake, beach and (Tiger Woods) Go ...
From $828 per night (USD)Expedia
From $101 per night (USD)VRBO
Peaceful place Great location food markets transportation downtown lake Michigan
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay. Great location steps away from food markets Great transporta ...
From $101 per night (USD)VRBO
From $163 per night (USD)VRBO
The Hyde Park Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this calm, stylish space. We hope to welcome you to the Hyde Park Haven and have the experience o ...
From $163 per night (USD)VRBO
From $173 per night (USD)VRBO
Guest Studio with private full bathroom, linen and towels are provided.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The studio is on the first floor, no need to climb stairs. The guest notebook is on the desk, it has Wi-fi info, lock se ...
From $173 per night (USD)VRBO
From $124 per night (USD)Expedia
Wonderful Three Bedroom Condo in Woodlawn
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
East Woodlawn. Recently renovated three bed, two bath condo on the second floor. Stainless steel appliances. Central air ...
From $124 per night (USD)Expedia
From $290 per night (USD)VRBO
Large Home, Full in-home Gym, washer\/dryer, flat Screen TVs, WiFi, and MORE!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Everything you need under one roof. Full in-house gym with stationary bike, weights, weighted Hula Hoop, dedicated Yoga ...
From $290 per night (USD)VRBO
From $5 per night (USD)Expedia
5 mins from Chicago U. Family sized apt with balcony & back yard. Free parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Comfortable, spacious, clean, and quiet apartment home. A lot of natural sunlight. 5 Minutes from Chicago U and the New ...
From $5 per night (USD)Expedia
From $93 per night (USD)VRBO
Chic Chicago Abode: Steps from Magnificent Mile!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
Discover the best of the Windy City with a stay at this charming 3-bedroom, 1.5-bathroom home. Immerse yourself in the v ...
From $93 per night (USD)VRBO
From $303 per night (USD)Expedia
Beautiful newly renovated townhome, very quite, safe, centralized location.\n
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
You will experience, high end appliances, glass staircase, wood floors throughout, secluded private backyard, T.V’s and ...
From $303 per night (USD)Expedia
From $284 per night (USD)VRBO
Charming 3BR Chicago Apt in Prime Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is located in the desirable Southside neighborhood of Chicago. The area is known for its vibrant culture, diver ...
From $284 per night (USD)VRBO
From $147 per night (USD)Expedia
The MOD Suite: Quaint family abode near UChicago, Lakeshore Dr. & DuSable Museum
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Unwind with the whole family at the Mod suite! This stylish and cozy 3-bedroom, 2-bathroom suite is located just steps ...
From $147 per night (USD)Expedia
From $193 per night (USD)VRBO
University of Chicago Condo-Upgraded and Spacious w\/Parking
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Remodeled unit with open floorplan, hardwd ...
From $193 per night (USD)VRBO
From $88 per night (USD)Expedia
Chicago Hi-Rise Lakeside Living in Spacious Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Very quiet, circa 1928, elegant building with doorman, owned and decorated by an art collector. Walking distance from: t ...
From $88 per night (USD)Expedia
From $297 per night (USD)VRBO
Great Location! 15 Min from DT -Historic Hyde Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
This spacious apartment is nestled in the beautiful Hyde Park neighborhood of Chicago - home to former President Barack ...
From $297 per night (USD)VRBO
From $288 per night (USD)Expedia
Vibrant 4BR Haven in Historic Hyde Park, Near University of Chicago
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This spacious apartment is nestled in the beautiful Hyde Park neighborhood of Chicago, home to former President Barack O ...
From $288 per night (USD)Expedia
From $180 per night (USD)VRBO
The Chic Urban Oasis Near the Lake!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our Urban Oasis located in Chicago's Historic Southshore! Only a 15 min drive to Downtown & a 5 min walk to t ...
From $180 per night (USD)VRBO
From $356 per night (USD)VRBO
Cozy Modern, 3BRS and 1BA. 5mins from Hyde Park tourist attractions
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This is a lovely 3 bedroom apartment. It’s located on a nice quiet block/neighborhood. Property is 5minutes from the Hyd ...
From $356 per night (USD)VRBO
From $452 per night (USD)VRBO
Luxury Stay on UChicago Campus 11 min walk to hospitals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful and tastefully decorated 3-bed, 2-bath condo on the prestigious University of Chicago campus, near hospitals, ...
From $452 per night (USD)VRBO
From $628 per night (USD)Expedia
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to our beautiful house UChicago campus house in the historic Hyde Park neighborhood of Chicago. This wonderful v ...
From $628 per night (USD)Expedia
From $171 per night (USD)VRBO
3 Bedroom 2 Bath beauty located steps away from Rainbow Beach, Metra stop, CTA.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This delightful apartment is the perfect home base for your trip to Chicago. With 3 cozy bedrooms, including 2 queen bed ...
From $171 per night (USD)VRBO
From $229 per night (USD)Expedia
Luxury Chic Condo Near Hot Attractions w\/FastWi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this spacious "Home Away from Home" fully equipped with all you need for your comfort & enjoyment. Each of th ...
From $229 per night (USD)Expedia
From $459 per night (USD)VRBO
Near Lakefront! Minutes from the beach, museum, and 2 golf courses.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Home away from home in this vintage, modern Greystone. Very comfortable living space with all the amenities you need to ...
From $459 per night (USD)VRBO
From $377 per night (USD)VRBO
Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
LOOK FOR THE GREEN DOOR BLACKS IN GREEN LAUNCHES NEXT LEVEL TOURISM IN WOODLAWN In homage to the legendary "Green Boo ...
From $377 per night (USD)VRBO
From $248 per night (USD)VRBO
Charming 3-bedroom apartment with AC, WiFi in phenomenal Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Chicago at this lovely apartment. With 3 bedrooms, including 1 queen bed, 1 child bed, and 1 full bed, this wo ...
From $248 per night (USD)VRBO
Click For PricingExpedia
Woodlawn LUXE! Welcome Home! 4 bedroom condo!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Come enjoy this newly renovated LUXE 4 bedroom 1 bathroom condo with all the bells and whistles on the entire second flo ...
Click For PricingExpedia
From $334 per night (USD)VRBO
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Chicago from this 2-bed, 2-bath condo. The space offers a lovely living room with a sofa that can ...
From $334 per night (USD)VRBO
From $201 per night (USD)Expedia
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Looking for a peaceful gem that's close to everything, University of Chicago, Jackson Park, Lakefront w/ easy access to ...
From $201 per night (USD)Expedia
From $213 per night (USD)VRBO
Modern East Woodlawn Apartment!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful 2-bedroom, 1-bath modern apartment in the thriving neighborhood of East Woodlawn. Walking distance to the new ...
From $213 per night (USD)VRBO
From $90 per night (USD)VRBO
Musician's Quarters\n\nChicago Jazz , Season discount
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Host Chester of Musicians Quarters is offering a Super Cheap BACK TO SCHOOL OFFER. $79 PER NIGHT. From August 21st to Au ...
From $90 per night (USD)VRBO
From $334 per night (USD)VRBO
Spacious 3-bedroom, one-level condo in beautiful Chicago.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this condo in picturesque Chicago. This beautiful rental features 3 queen beds spread across 3 bedrooms, ensur ...
From $334 per night (USD)VRBO
From $110 per night (USD)Expedia
Chicago Apt 3 Mi to Lake Michigan!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
10 Mi to Downtown Chicago | Private Deck | 1,875 Sq Ft Get to know the Windy City up close and personal while staying a ...
From $110 per night (USD)Expedia
From $228 per night (USD)VRBO
Cozy 3BR Hyde Park Oasis Near UChi, Shops & Dining
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Explore our home in Chicago's vibrant Southside neighborhood, renowned for its rich culture, diverse dining options, and ...
From $228 per night (USD)VRBO
From $161 per night (USD)Expedia
Beautiful 1BR Home in Historic Hyde Park Near University of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Hyde Park's rich history and cultural diversity. Nestled on Chicago's south side, this vibrant neighborhood is ...
From $161 per night (USD)Expedia
From $202 per night (USD)VRBO
2BR Modern APT Near University of Chicago & Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located next to the University of Chicago campus. Nestled in the beautiful Hyde Park neighborhood of Chicago - home to f ...
From $202 per night (USD)VRBO
From $217 per night (USD)Expedia
Prime Location: Spacious Unit Near University Of Chicago & Dining
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Located next to the University of Chicago campus. Nestled in the beautiful Hyde Park neighborhood of Chicago - home to f ...
From $217 per night (USD)Expedia
From $137 per night (USD)VRBO
A Chic 8th Floor Studio Inside Vintage Style Building With Spectacular Lake View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Here’s to your perfect getaway on the South Shore of Lake Michigan in Chicago which is located only minutes from the hea ...
From $137 per night (USD)VRBO
From $204 per night (USD)Expedia
Chic 3-bedroom corporate apartment with WiFi, AC in lovely Chicago.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a peaceful stay at this awesome 3-bedroom corporate apartment in Chicago. With 2 queen beds and 1 twin bed, guests ...
From $204 per night (USD)Expedia
From $90 per night (USD)VRBO
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<b>Experience Chicago</b> Experience Chicago in this fabulous, all modern 3-bedroom 3-bath condo near Hyde Park, The Ob ...
From $90 per night (USD)VRBO