Vacation rentals in Grant Park, Chicago

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Top-rated vacation rentals in Grant Park, Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Little Italy

4.99 out of 5 average rating, 776 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.

Dec 11 – 18

$111 per night
Superhost

Guest suite in McKinley Park

4.84 out of 5 average rating, 193 reviews

Vintage Suite Home Chicago by Sox/Park/Transit

Guest suite in an 1890 Worker's Cottage with plenty of character, originally built for laborers in the Chicago Stockyards. This quiet neighborhood is a respite from city buzz, just 20 min from the Loop. Your space has great natural light, 2 comfy beds (1 folds to a couch), private bath, flexible work/dining area, super-fast WiFi, and a kitchen with all the essentials. Private entry via back door. Free parking. Get downtown in 4 stops by train or any of 5 nearby buses. Se habla español.

Sep 2 – 9

$82 per night
Guest favorite

Guest suite in East Pilsen

4.93 out of 5 average rating, 111 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.

Jun 18 – 25

$97 per night

Popular amenities for Grant Park, Chicago vacation rentals

Stay near Grant Park, Chicago's top sights

The Art Institute of Chicago1,159 locals recommend
Buckingham Fountain219 locals recommend
Butler Field7 locals recommend
Agora3 locals recommend
Petrillo Music Shell5 locals recommend
Museum Campus/11th St. station3 locals recommend

Other great vacation rentals in Grant Park, Chicago

Guest favorite

Home in Bridgeport

4.95 out of 5 average rating, 111 reviews

Cozy & Modern Chic Full House in Trendy Bridgeport

Feb 8 – 15

$102 per night
Guest favorite

Apartment in Humboldt Park

4.98 out of 5 average rating, 102 reviews

Humboldt Park Loft

Sep 11 – 18

$106 per night
Superhost

Apartment in Pilsen Historic District

4.86 out of 5 average rating, 230 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Jul 12 – 19

$60 per night
Guest favorite

Home in West Loop

4.97 out of 5 average rating, 316 reviews

Cozy garden apartment historic Jackson Bvld.

Mar 9 – 14

$145 per night
Guest favorite

Home in Pilsen Historic District

4.95 out of 5 average rating, 309 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

Mar 6 – 13

$123 per night
Superhost

Apartment in Chicago

4.84 out of 5 average rating, 126 reviews

Perfect Private Getaway in Perfect Pilsen

Jul 23 – 30

$83 per night
Superhost

Apartment in Chicago

4.8 out of 5 average rating, 15 reviews

Cozy Condo near Downtown Chicago

Oct 21 – 28

$137 per night
Superhost

Apartment in Pilsen Historic District

4.91 out of 5 average rating, 22 reviews

15min/Loop, PilsenTreasure, Sunny1BR Apt w/Parking

Aug 22 – 29

$112 per night
Guest favorite

Apartment in Chicago

4.8 out of 5 average rating, 15 reviews

Cozy Pilsen Apartment

Aug 13 – 20

$95 per night
Guest favorite

Apartment in Bridgeport

4.87 out of 5 average rating, 31 reviews

Your Perfect Spot :)-With Memory Foam Mattress!

Dec 27 – Jan 3

$92 per night
Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 16 reviews

Travel To Chicago New City

Nov 19 – 26

$90 per night
Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 57 reviews

Location! Location! Location!

Jun 12 – 19

$110 per night

Quick stats about vacation rentals in Grant Park, Chicago

Total rentals

80 properties

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

3.1K reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Grant Park