Chicago River vacation rentals

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Top-rated vacation rentals in Chicago River

Guests agree: these vacation rentals 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

R2,441 ZAR per night
Superhost

Apartment in The Loop

4.86 out of 5 average rating, 187 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building has a pool and an amazing outdoor rooftop terrace with 360 degree vi

Nov 14 – 21

R9,478 ZAR 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

R2,137 ZAR per night

Popular amenities for Chicago River vacation rentals

Other great vacation rentals in Chicago River

Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 122 reviews

Modern Apt with style & comfort in Pilsen Chicago

May 13 – 18

R2,560 ZAR per night
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

R2,245 ZAR per night
Guest favorite

Guest suite in Chicago

5.0 out of 5 average rating, 290 reviews

Private Lincoln Square one bed+bath studio apt.

Sep 15 – 22

R2,658 ZAR per night
Guest favorite

Home in West Town

4.95 out of 5 average rating, 166 reviews

Paradise on the Park

Nov 30 – Dec 7

R2,818 ZAR per night
Guest favorite

Loft in Lake View

4.96 out of 5 average rating, 409 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

Dec 19 – 26

R2,878 ZAR per night
Guest favorite

Apartment in West Loop

4.99 out of 5 average rating, 351 reviews

Peaceful River West Apt with free parking

Apr 7 – 14

R5,125 ZAR per night
Guest favorite

Condo in Chicago

4.95 out of 5 average rating, 432 reviews

Unique Lincoln Park Duplex Apt

May 21 – 28

R3,489 ZAR per night
Guest favorite

Guest suite in Lake View

4.91 out of 5 average rating, 355 reviews

Contemporary, private suite w fireplace

Dec 3 – 10

R1,482 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 293 reviews

Redesigned Lower Level Studio in Historic Building

Sep 3 – 10

R3,289 ZAR per night
Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 226 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Oct 30 – Nov 6

R2,623 ZAR per night
Guest favorite

Guest suite in West Loop

4.84 out of 5 average rating, 133 reviews

West Loop 2 bedroom with outdoor space

Apr 20 – 27

R2,493 ZAR 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

R2,689 ZAR per night

Other great vacation rentals in Chicago River

Superhost

Home in Near North Side

4.85 out of 5 average rating, 80 reviews

503LOFT | Top Floor 5 BED, 2 BA Downtown Loft

Feb 18 – 25

R5,002 ZAR per night
Guest favorite

Apartment in Near North Side

4.99 out of 5 average rating, 98 reviews

*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

R1,861 ZAR per night
Guest favorite

Apartment in West Town

5.0 out of 5 average rating, 32 reviews

Cozy Studio in Perfect Location

Nov 7 – 14

R2,749 ZAR per night
Guest favorite

Apartment in Near North Side

4.97 out of 5 average rating, 30 reviews

53 Floor MagMile Penthouse Views, Balcony, Pool

Jan 20 – 27

R8,026 ZAR per night
Superhost

Apartment in The Loop

5.0 out of 5 average rating, 6 reviews

STUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING

Dec 22 – 29

R14,680 ZAR per night
Guest favorite

Guest suite in West Town

4.92 out of 5 average rating, 39 reviews

Renovated basement studio w/ independent entrance

Oct 21 – 28

R2,463 ZAR per night
Guest favorite

Apartment in River North

4.92 out of 5 average rating, 73 reviews

Cloud9 |Social club| Motion Studio|The Hamilton

May 4 – 11

R8,516 ZAR per night
Guest favorite

Condo in Lincoln Park

4.94 out of 5 average rating, 33 reviews

Spacious Apartment in Chicago

R2,395 ZAR per night
Superhost

Apartment in Chicago

4.81 out of 5 average rating, 57 reviews

McCormick Place Studio/parking/sleeps up to 4

Feb 16 – 23

R1,737 ZAR 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

R2,444 ZAR per night
Superhost

Condo in Lincoln Park

4.8 out of 5 average rating, 80 reviews

Stylish Stay Steps from Old Town + Lincoln Park

Dec 6 – 13

R2,691 ZAR per night
Guest favorite

Condo in Gold Coast

4.96 out of 5 average rating, 50 reviews

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Jun 22 – 29

R10,599 ZAR per night

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