Vacation rentals in Grant Park, Chicago

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Top-rated vacation rentals in Grant Park, Chicago

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Guest favourite

Guesthouse in Little Italy

4.99 out of 5 average rating, 783 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Oct. 25 – Nov. 1

$259 CAD per night

Guest favourite

Guest suite in Bridgeport

4.96 out of 5 average rating, 182 reviews

Clean, Cozy, Comfortable Studio Near Downtown

You'll feel right at home in our private studio in Bridgeport, a quiet Chicago neighborhood with a rich history. Just 5 miles from downtown! Easily accessible from Midway and O'Hare, 1 mile from White Sox stadium (Guaranteed Rate Field), 15 minutes by car from the heart of the Loop, and convenient to McCormick Place, IIT, UIC, and Chinatown. You can easily walk to great coffee, diverse restaurants, art galleries, and more, while getting a taste of an authentic working-class Chicago neighborhood.

Jul. 3 – 10

$227 CAD per night

Guest favourite

Guest suite in East Pilsen

4.93 out of 5 average rating, 114 reviews

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Welcome to a brand new, entirely private, spacious and peaceful oasis in East Pilsen-UIC with its own smartlock/entry system and self check in. Located at the intersection of some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Amenities: Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, Keurig coffeemaker, hair dryer, iron and toiletries. The best part... a set of glass doors that open to a lovely private deck.

Jul. 10 – 17

$218 CAD per night

Guest favourite

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Oct. 29 – Nov. 5

$167 CAD per night

Guest favourite

Apartment in Humboldt Park

4.98 out of 5 average rating, 106 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Oct. 8 – 15

$224 CAD per night

Guest favourite

Apartment in Chicago

4.85 out of 5 average rating, 160 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

Guest favourite

Apartment in West Town

4.96 out of 5 average rating, 262 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

Dec. 23 – 30

$193 CAD per night

Guest favourite

Apartment in Pilsen Historic District

4.85 out of 5 average rating, 233 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond.

Aug. 15 – 22

$139 CAD per night

Guest favourite

Apartment in Chicago

4.98 out of 5 average rating, 128 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Jul. 12 – 19

$248 CAD per night

Guest favourite

Guest suite in Bridgeport

4.94 out of 5 average rating, 123 reviews

Comfortable & Cozy in Bridgeport

Cozy in-law apartment (garden-level) in Chicago's Bridgeport neighborhood. Great for a couple, a single person that is "working from home," or young friends. Unique touches like local art (including a hand-painted shower curtain), equipped kitchen, and a mini library out front in case you forgot your book! In a nice, quiet neighborhood that is close to Chinatown, Pilsen, Sox Park, Midway, and McCormick Place. Chicago Registration Number: R21000062030

Jun. 2 – 7

$227 CAD per night

Guest favourite

Guest suite in Bronzeville

4.94 out of 5 average rating, 154 reviews

Bronzeville Beauty: Modern Style + Historic Charm

Come relax and take in Chicago's historic Bronzeville neighborhood. Stay in the bright and sunny garden unit of a fully renovated landmarked home built in 1887. We are located across from a neighborhood park with excellent access to CTA transit. Walkable to Lake Michigan, Lakefront Trail, White Sox stadium, IIT. Very close to McCormick Place, Hyde Park, and Chinatown. If you drive, free street parking is readily available in front of our home.

Sep. 19 – 26

$237 CAD per night

Guest favourite

Home in Bridgeport

4.95 out of 5 average rating, 120 reviews

Cozy & Modern Chic Full House in Trendy Bridgeport

Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Jan. 9 – 16

$222 CAD per night