Downtown Chicago vacation rentals

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Top-rated vacation rentals in Downtown Chicago

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Guest favorite

Guesthouse in Little Italy

4.99 out of 5 average rating, 784 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.

Feb 15 – 22

€ 165 per night

Guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 297 reviews

Redesigned Lower Level Studio in Historic Building

The space is very comfortable, quiet and cozy. There are new cabinets, granite counter tops, all new appliances and a washer and dryer. Guests sleep on a king size tempur-pedic mattress or a queen size trundle style pull out sofa. There is hi-speed wi-fi, cable TV (Showtime), 55' flat screen TV and a wood burning fireplace. The bathroom is immaculate and includes a full bathtub with shower. This is a private apartment and you will have access to the entire suite. There is a back and front door with adequate lighting and easy access for guests. My family and I live next door and I will be available at our guests convenience. I am happy to provide any information, recommendations, directions etc.. I am easy to reach and am always available but will not intrude on our guests privacy. This unit is on a beautiful tree lined street in the heart of Old Town, close to St. Michael's Church, Steppenwolf Theater, and the Second City Improv Theater. The location allows for easy access to all of Chicago by either train, bus, or car. The blue and brown line train stations are within walking distance. Street parking is readily available and no permits are necessary. A Chicago Cab or Uber can get you to Milleniumm Park in approx. 15 minutes. Four adults can comfortably stay in this unit. The king size tempur_pedic mattress is the pinnacle of comfort and the queen size trundle style pull out sofa is comparable to sleeping on an actual queen size mattress. The queen size bed could comfortably fit 3 children. There is street parking readily available but I can provide an assigned space behind the building if necessary, for additional cost.

Oct 3 – 10

€ 185 per night

Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 293 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

Sep 17 – 24

€ 174 per night

Guest favorite

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 17 – 24

€ 152 per night

Guest favorite

Apartment in Avondale

4.97 out of 5 average rating, 117 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Jul 11 – 18

€ 150 per night

Guest favorite

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*

Sep 13 – 20

€ 115 per night

Guest favorite

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 10 – 17

€ 154 per night

Guest favorite

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.

Apr 15 – 22

€ 134 per night

Guest favorite

Loft in Lake View

4.96 out of 5 average rating, 417 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Jan 15 – 22

€ 183 per night

Guest favorite

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 9 – 16

€ 171 per night

Guest favorite

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.

Dec 11 – 18

€ 153 per night

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 140 reviews

Charming Gold Coast One-Bedroom Near Downtown!

Perfect Gold Coast studio near downtown, the lake and everything else! We are nestled in the Gold Coast in an excellent location. Public Transportation, restaurants, shops, museums and grocery stores are all steps away! The apartment is within an art deco style mid rise and has everything you need to be your home away from home while you're visiting the city of broad shoulders. Chicago Shared Housing Registration Number: R21000073420

Mar 6 – 13

€ 149 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Downtown Chicago vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Downtown Chicago

Guest favorite

Apartment in Lincoln Park

4.83 out of 5 average rating, 208 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

Jan 10 – 17

€ 135 per night

Superhost

Apartment in East Rogers Park

4.88 out of 5 average rating, 104 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

Jan 23 – 30

€ 142 per night

Guest favorite

Apartment in Uptown

4.96 out of 5 average rating, 265 reviews

Cozy loft in Chicago's Uptown

Oct 15 – 22

€ 133 per night

Guest favorite

Apartment in Pilsen Historic District

4.85 out of 5 average rating, 233 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Aug 15 – 22

€ 96 per night

Guest favorite

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Jul 6 – 13

€ 141 per night

Guest favorite

Apartment in Little Italy

4.98 out of 5 average rating, 198 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

Jan 7 – 14

€ 216 per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 237 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

Dec 26 – Jan 2

€ 133 per night

Superhost

Apartment in Irving Park

4.86 out of 5 average rating, 100 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

Apr 19 – 26

€ 108 per night

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Downtown Chicago condo rentals

Superhost

Condo in West Town

4.87 out of 5 average rating, 107 reviews

Spacious Duplex in Great Location

Aug 20 – 27

€ 153 per night

Guest favorite

Condo in Lincoln Park

4.95 out of 5 average rating, 438 reviews

Unique Lincoln Park Duplex Apt

Sep 26 – Oct 3

€ 223 per night

Superhost

Condo in West Town

4.86 out of 5 average rating, 435 reviews

Humboldt Park Traveler's Lodge

May 20 – 27

€ 165 per night

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 122 reviews

3D Tour! Designer Condo near Logan Square

Sep 19 – 26

€ 177 per night

Guest favorite

Condo in Chicago

4.88 out of 5 average rating, 234 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Sep 7 – 14

€ 192 per night

Guest favorite

Condo in East Rogers Park

4.93 out of 5 average rating, 186 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Oct 16 – 23

€ 128 per night

Guest favorite

Condo in Logan Square

4.98 out of 5 average rating, 232 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Oct 27 – Nov 3

€ 233 per night

Guest favorite

Condo in North Center

4.91 out of 5 average rating, 120 reviews

Spacious & Modern Family Friendly North Center Apt

Jan 26 – Feb 2

€ 190 per night

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Other great vacation rentals in Downtown Chicago

Guest favorite

Townhouse in Near West Side

4.85 out of 5 average rating, 275 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Nov 3 – 10

€ 121 per night

Guest favorite

Guest suite in Chicago

4.97 out of 5 average rating, 361 reviews

Private suite in Lincoln Square

Dec 30 – Jan 6

€ 132 per night

Guest favorite

Guest suite in Lake View

4.91 out of 5 average rating, 358 reviews

Contemporary, private suite w fireplace

Mar 26 – Apr 2

€ 96 per night

Guest favorite

Loft in Forest Park

4.96 out of 5 average rating, 463 reviews

Walk to Oak Park from a Bright Madison Street Loft

Dec 9 – 16

€ 142 per night

Guest favorite

Guest suite in Lake View

4.95 out of 5 average rating, 175 reviews

1 mile from Wrigley Field

Sep 5 – 12

€ 184 per night

Guest favorite

Home in West Loop

4.97 out of 5 average rating, 318 reviews

Cozy garden apartment historic Jackson Bvld.

Jan 21 – 26

€ 226 per night

Guest favorite

Guest suite in Chicago

4.93 out of 5 average rating, 172 reviews

Bike the Lakefront from a Sleek Urban Retreat

Sep 8 – 15

€ 145 per night

Guest favorite

Guest suite in Irving Park

4.99 out of 5 average rating, 136 reviews

BnB on Grace Street - Modern 2-Bedroom Guest Suite

Oct 15 – 22

€ 156 per night

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Frequently Asked Questions

How is the weather in Downtown Chicago?
Downtown Chicago experiences a diverse climate. Summers can be hot, typically reaching 85°F (29°C), while winter temperatures can drop to around 20°F (-6°C), often accompanied by snow. The transitional seasons, spring and fall, offer more moderate weather, making them pleasant times to visit.
What are some of the best things to do in Downtown Chicago?
There's no shortage of activities in Downtown Chicago. Explore the Art Institute of Chicago, walk alongside the Chicago River, or enjoy a stroll in Millennium Park. You can also marvel at the city's skyline from the Willis Tower's Skydeck or take a boat cruise on Lake Michigan.
What is the best time of year to visit Downtown Chicago?
The summer months, from June to August, are a great time to explore Downtown Chicago as the city comes alive with a range of cultural events including Lollapalooza, the Chicago Air and Water Show, and the Jazz Festival. However, the city also offers distinctive charm during the winter season, with events like the Magnificent Mile Lights Festival and the Winter WonderFest.
What are the best places to stay in Downtown Chicago?
Guests enjoy staying in several areas in Downtown Chicago. The Loop, Chicago's central business district, is known for its bustling atmosphere and close proximity to many attractions. River North, with its art galleries and fashion outlets, is also popular. Streeterville, near Navy Pier and Magnificent Mile, is another preferred location.
What are the best places to visit in Downtown Chicago?
There are many popular places to visit in Downtown Chicago. These include the Navy Pier, with its iconic Ferris wheel, the Art Institute of Chicago, known for its impressive collection, and the historic Chicago Theatre. Don't miss a walk down the Magnificent Mile for shopping and dining.
What are some hiking trails in Downtown Chicago?
While Downtown Chicago is primarily urban, there are lovely trails to explore. The 18-mile (29 km) Lakefront Trail along Lake Michigan is a favorite among locals and visitors. The Chicago Riverwalk also provides a scenic urban hike through the heart of the city.
What are some family activities to do in Downtown Chicago?
Families in Downtown Chicago can explore a multitude of engaging activities. Visit the Shedd Aquarium or the Field Museum for an educational outing, enjoy outdoor fun at Maggie Daley Park, or discover the wonders of space at the Adler Planetarium.
What are some of the best day trip ideas in Downtown Chicago?
For day trips, consider exploring the natural beauty of the Chicago Botanic Garden or the historical architecture in Oak Park, both within a short drive from Downtown. Alternatively, the Indiana Dunes National Park, 50 miles (80 km) away, offers an escape to nature.

Downtown Chicago vacation rentals

Top-rated vacation rentals in Downtown Chicago

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Downtown Chicago vacation rentals

Other great vacation rentals in Downtown Chicago

Apartment in Lincoln Park

Apartment in East Rogers Park

Apartment in Uptown

Apartment in Pilsen Historic District

Apartment in Lincoln Square

Apartment in Little Italy

Apartment in Chicago

Apartment in Irving Park

Downtown Chicago condo rentals

Condo in West Town

Condo in Lincoln Park

Condo in West Town

Condo in Chicago

Condo in Chicago

Condo in East Rogers Park

Condo in Logan Square

Condo in North Center

Other great vacation rentals in Downtown Chicago

Townhouse in Near West Side

Guest suite in Chicago

Guest suite in Lake View

Loft in Forest Park

Guest suite in Lake View

Home in West Loop

Guest suite in Chicago

Guest suite in Irving Park

Frequently Asked Questions

How is the weather in Downtown Chicago?

What are some of the best things to do in Downtown Chicago?

What is the best time of year to visit Downtown Chicago?

What are the best places to stay in Downtown Chicago?

What are the best places to visit in Downtown Chicago?

What are some hiking trails in Downtown Chicago?

What are some family activities to do in Downtown Chicago?

What are some of the best day trip ideas in Downtown Chicago?

Destinations to explore