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, 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

R2,751 ZAR per night

Guest favorite

Guest suite in Chicago

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

R2,679 ZAR per night

Guest favorite

Guest suite in Chicago

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

R2,223 ZAR 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

R2,315 ZAR 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 8 – 15

R2,339 ZAR 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.

Dec 23 – 30

R1,949 ZAR per night

Guest favorite

Loft in Lake View

4.96 out of 5 average rating, 416 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.

Feb 5 – 12

R2,901 ZAR 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

R2,715 ZAR 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.

Jan 9 – 16

R2,263 ZAR 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

Jan 28 – Feb 4

R1,979 ZAR per night

Guest favorite

Townhouse in Chicago

4.85 out of 5 average rating, 275 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS.

Nov 3 – 10

R1,785 ZAR per night

Superhost

Apartment in Chicago

4.84 out of 5 average rating, 175 reviews

The Cottage

Nice cozy and welcoming place. Easy access to public transportation. 10 to 15 minutes from downtown, museums, Sox and Bulls stadiums. Located in the colorful and lively neighborhood of Pilsen and close to Little Italy. Smart devices installed for easy check-in and safety (extremely accurate and sensitive smoke detector warning all occupants of possible problems). Guest wifi included with some feel home amenities.

Sep 27 – Oct 4

R1,473 ZAR 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 Chicago

4.92 out of 5 average rating, 185 reviews

Taj Ma-small at Wrigley

Feb 10 – 17

R2,313 ZAR per night

Guest favorite

Apartment in Chicago

4.99 out of 5 average rating, 193 reviews

Explore Lincoln Park from a Polished Apartment

Jan 16 – 23

R3,179 ZAR per night

Guest favorite

Apartment in West Town

4.92 out of 5 average rating, 326 reviews

Bright, Modern Apartment in a Vintage Greystone

Jan 16 – 23

R2,718 ZAR per night

Superhost

Apartment in East Rogers Park

4.88 out of 5 average rating, 104 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

Feb 23 – Mar 2

R2,269 ZAR per night

Guest favorite

Apartment in West Town

4.89 out of 5 average rating, 473 reviews

iKlektik House Chicago / Robin

Dec 3 – 10

R2,621 ZAR per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 201 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Nov 17 – 24

R2,351 ZAR per night

Guest favorite

Apartment in Pilsen Historic District

4.86 out of 5 average rating, 232 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Aug 15 – 22

R1,445 ZAR per night

Guest favorite

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Jul 2 – 9

R2,172 ZAR per night

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Downtown Chicago home rentals

Guest favorite

Home in West Loop

4.97 out of 5 average rating, 318 reviews

Cozy garden apartment historic Jackson Bvld.

Jan 22 – 27

R3,464 ZAR per night

Guest favorite

Home in Chicago

4.96 out of 5 average rating, 316 reviews

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

Jan 28 – Feb 4

R2,677 ZAR per night

Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 237 reviews

Private apartment with retro vibe

Oct 5 – 12

R1,786 ZAR per night

Guest favorite

Home in West Town

4.95 out of 5 average rating, 171 reviews

Paradise on the Park

Oct 1 – 8

R3,239 ZAR per night

Guest favorite

Home in Wicker Park

4.96 out of 5 average rating, 200 reviews

Division St Designer Home In Heart of Wicker Park

May 20 – 25

R5,143 ZAR per night

Guest favorite

Home in Uptown

4.89 out of 5 average rating, 332 reviews

Private 3rd Floor Apartment

Dec 8 – 15

R2,399 ZAR per night

Guest favorite

Home in Lake View

4.98 out of 5 average rating, 205 reviews

Wrigleyville Southport Studio

Dec 13 – 20

R3,029 ZAR per night

Guest favorite

Home in Avondale

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

Nov 13 – 20

R1,929 ZAR per night

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Downtown Chicago condo rentals

Superhost

Condo in West Town

4.87 out of 5 average rating, 106 reviews

Spacious Duplex in Great Location

Aug 21 – 28

R2,408 ZAR per night

Guest favorite

Condo in Uptown

4.92 out of 5 average rating, 110 reviews

Stunning, Spacious, & Sun-Soaked 1br Uptown Condo

Jan 19 – 26

R2,673 ZAR per night

Guest favorite

Condo in Lincoln Square

4.98 out of 5 average rating, 329 reviews

Lincoln Square Gem!

Oct 4 – 11

R2,766 ZAR per night

Guest favorite

Condo in East Rogers Park

4.93 out of 5 average rating, 186 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Jan 7 – 14

R1,865 ZAR per night

Guest favorite

Condo in Chicago

4.95 out of 5 average rating, 437 reviews

Unique Lincoln Park Duplex Apt

Sep 26 – Oct 3

R3,516 ZAR per night

Guest favorite

Condo in West Town

4.88 out of 5 average rating, 234 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Sep 5 – 12

R2,970 ZAR per night

Superhost

Condo in West Town

4.86 out of 5 average rating, 435 reviews

Humboldt Park Traveler's Lodge

May 20 – 27

R3,007 ZAR per night

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 122 reviews

3D Tour! Designer Condo near Logan Square

Sep 17 – 24

R2,783 ZAR 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

Houses

Apartments

Hotels

Popular amenities for Downtown Chicago vacation rentals

Other great vacation rentals in Downtown Chicago

Apartment in Chicago

Apartment in Chicago

Apartment in West Town

Apartment in East Rogers Park

Apartment in West Town

Apartment in Cicero

Apartment in Pilsen Historic District

Apartment in Lincoln Square

Downtown Chicago home rentals

Home in West Loop

Home in Chicago

Home in Berwyn

Home in West Town

Home in Wicker Park

Home in Uptown

Home in Lake View

Home in Avondale

Downtown Chicago condo rentals

Condo in West Town

Condo in Uptown

Condo in Lincoln Square

Condo in East Rogers Park

Condo in Chicago

Condo in West Town

Condo in West Town

Condo in Chicago

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