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Chicago vacation rentals

Vakantieverhuur in Chicago van de eigenaar — vergelijk huizen, appartementen en cabins, stuur berichten naar geverifieerde hosts en boek direct. Je ziet alle kosten voordat je betaalt.

Chicago draws visitors with attractions like Millennium Park, Navy Pier, the Art Institute of Chicago, and Wrigley Field. The city's vibrant cultural scene includes events such as Lollapalooza, the Chicago Blues Festival, and iconic architecture tours. Houfy connects you directly with local hosts in Chicago, allowing bookings that keep costs low. Explore neighborhood lofts, downtown apartments, and lakeside condos across Lincoln Park, Lakeview, and the Loop. Summer along Lake Michigan is ideal for outdoor festivals and cruising the Chicago River.

Best beoordeelde vakantiehuizen in Chicago

Blader door de hoogst beoordeelde vakantie-eigendommen in Chicago.

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bd·2½ ba
4.9· 106

$ 885,00 USD totaal voor 3 nachten

8–11 nov 2026

We loved our stay at this exquisite & perfectly curated home. Perfect location, within walking distance to the school, supermkts & public transportation. We were definitely blown away & mesmerized as we walked into each area and room in the home. We even took notes for our own future home decorations. The artwork is representative of Black history, which goes perfectly with the home’s location of South Chicago. While at the same time, walking through the home takes you on an int’l trip. It has a very homey feel; the Teens loved it, especially playing Michael Jackson from the fridge while we all took in the decor. The feedback that we would give is to please provide add’l blankets for the bedding & to please run the gas heater a day before to avoid the weird smell that may come out of it, if it has not been turned on for a while. Elisabeth & Juaquan were very attentive and Juaquan came right over when we informed him of the funny smell. We will definitely stay again, LONGER. Thank you!?
V. · Verblijf op november 2025

Hyde Park 2BR UChicago Medical Museums 20% OFF

2 bd·1 ba
5· 4
Fantastic place, and even better host
Fantastic place, and even better host, who was attentive to all my (small) needs. Very large apartment with everything you might need. Very close to UChicago, quiet neighborhood. I've stayed here 3x now, and will stay here again next time I'm in Chicago!
Tom · Verblijf op maart 2026

MFL 2 East

4 bd·3 ba
4.93· 120

$ 2.113,34 USD $ 1.827,39 USD totaal voor 3 nachten

9–12 nov 2026

Coming back to Chicago just for this place!
This whole trip was amazing thanks to Carole! She greeted us with a special Chicago beer and made us feel right at home. She knew so much about the city and had lots of recommendations for food, bars, transportation, etc. Honestly, if we had more time, I would've loved to sit down for a drink with her and her husband, Basil! Our Magic Factory Loft was incredible and perfect for our group of 11 girls. We could've fit at least three more, and maybe even more than that if needed. The place was just right for a big group, with the common areas like the kitchen and living room being just a big hangout space. And then we had three full bathrooms which was definitely appreciated. In the loft, we were able to sit around in a circle and play games, enjoy snacks, etc. without feeling like we were too cramped. Carole even left us a "decoration kit" to help with hanging decor around the place for our party! You can really tell how much effort they put into making this place look really nice and be as cozy as possible. The loft is in a great location. We never felt unsafe and we were able to walk to pretty much everywhere. We also had free parking right outside! Carole got us into two FAB restaurants that we definitely would not have gotten into otherwise. They ended up being the two best restaurants of the weekend and everyone was so happy. We honestly could not have asked for anything more. I literally want to go back to Chicago just so I can stay there again! We will be back -- thank you Carole and Basil!
E. W. · Verblijf op juli 2019

Modern Western Logan Square Flat Healy Metra Stop

2 bd·1 ba
4.75· 24

$ 478,58 USD totaal voor 3 nachten

8–11 nov 2026

My husband and I had a great visit to Logan Square and the Chicago area while staying at this location. The home was spotless, looked and functioned exactly as described, and had unique architectural features that made staying there a treat. We could walk to the Square, catch a ride with friends, and found parking pretty easy in the surrounding park/residential areas. Catching a ride share downtown is also very simple as the home is located near main arterial roads. We had no problem pre-scheduling a ride share to take us downtown during peak times, and to the airport early in the morning of our departure. The surrounding neighborhood is historic and classic Chicago which we appreciated. We stayed during the July 4 holiday weekend, and recommend visiting during this time for a full "Chicago experience" -- a mix of locals and tourists, with notably less traffic and other congestion compared to other major cities during this holiday weekend.
N. · Verblijf op juli 2024

MFL 3 East

4 bd·4 ba
4.99· 93

$ 2.738,67 USD $ 2.358,91 USD totaal voor 3 nachten

8–11 nov 2026

Excellent location, excellent stay, excellent service
We were a group of 8 women staying for 5 days at this property in a combination writing retreat/ladies getaway. We had an absolutely fantastic experience in the loft and would 100% recommend it to other groups, as well as stay again. The communication with Carole was top notch, including her meeting several requests that we had, as well as offering recommendations. We had everything we needed for the 5 days and were so happy throughout our entire stay. The location is top notch and just about anything you want is within a few blocks walk, from restaurants to Whole Foods to Target to a liquor store to casual shopping , entertainment and more. You can't ask for a better location! In addition, the loft is well insulated and the *only* outside noise that ever came to us was from fire engines going by. Otherwise, the loft was quiet and well-contained. With 4 bathrooms and 4 bedrooms, as well as a variety of beds/sleeping options, there's plenty of room for a large group. Possibly our only request would have been an additional sofa or longer sofas, as we did spend a lot of time at the loft and would have liked more lounging options/comfortable seating options (the dining room chairs are great for dining but not long-term seating/working). The kitchen was fully stocked with everything we needed in terms of utensils, pots, pans, etc for cooking, and there wer even a few random spices. One touch we absolutely loved was the bags of ice provided in the freezer. That's something I wouldn't have though tto ask for but would now love to see in every vacation rental we stay in. There was also some coffee, tea and sugar provided--a top notch service all the way! In short, this is a fantastic choice for your next vacation stay as a group, I can't recommend it highly enough, and I hope we get to experience Carole and Basil's hospitality again some day!
A. W. · Verblijf op september 2019

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3 bd·1 ba
4.92· 25

$ 613,35 USD totaal voor 3 nachten

8–11 nov 2026

Simiao was an incredibly responsive and hospitable host throughout our extended stay. She went above and beyond to help my mom and mother-in-law, who were visiting the U.S. for the first time and only speak Mandarin, feel comfortable and enjoy their experience. She recommended places to visit in the neighborhood, showed them how to use the laundry, and even created a step-by-step instructional video in Mandarin for them. Whenever we needed extra supplies, she had them ready for us right away. Her thoughtfulness and kindness made our stay even more enjoyable. We would definitely stay here again on our next visit.
P. · Verblijf op juli 2026

Large Cozy 3BR near UChicago Medical Midway Museum

3 bd·1 ba
5· 8
We had a great stay at Kenneth's! Lot of space, cozy and clean home, all amenities as described, great communication and easy on-street parking on the south side. Ken was a great host: very proactive, friendly, helpful, and had good communication regarding any questions we had during the stay. He was kind enough to accommodate our requests which made our trip (with 2 seniors) much less troublesome. Would gladly recommend his Airbnb.
B. · Verblijf op september 2024

Chicago Lakefront · Fire Pit Patio · Beach Across

1 bd·1 ba
5· 1

$ 467,00 USD $ 373,60 USD totaal voor 3 nachten

8–11 nov 2026

The apartment was perfect for our stay in Chicago. It was just a couple blocks from the train station, perfect for getting to Guaranteed Rate Field. Right across the street is the beach and there are plenty of stores and restaurants nearby. The hosts were great at communicating if we needed anything and very nice! The apartment was nice and clean! If you want the best of the city and Lake Michigan for a great price, stay here!
L. · Verblijf op mei 2026

Aanbevolen huizen in Chicago

Handpicked eigendommen waarvan wij denken dat je ze leuk zult vinden in Chicago.

Luxurious Condo in Top Rated Neighborhood

1 bd·1 ba
4.46· 28

$ 3.600,00 USD totaal voor 30 nachten

8 nov – 8 dec 2026

$ 1.484,11 USD totaal voor 3 nachten

8–11 nov 2026

$ 960,27 USD totaal voor 3 nachten

8–11 nov 2026

$ 4.469,80 USD totaal voor 30 nachten

8 nov – 8 dec 2026

$ 2.090,00 USD totaal voor 5 nachten

8–13 nov 2026

$ 606,82 USD totaal voor 3 nachten

8–11 nov 2026

$ 899,64 USD totaal voor 3 nachten

8–11 nov 2026

$ 498,62 USD totaal voor 3 nachten

8–11 nov 2026

Pet friendly vacation rentals in Chicago

Neem je harige vriend mee! Blader door huisdiervriendelijke woningen in Chicago.

$ 717,36 USD totaal voor 3 nachten

8–11 nov 2026

$ 649,61 USD totaal voor 3 nachten

8–11 nov 2026

$ 1.982,08 USD totaal voor 3 nachten

8–11 nov 2026

$ 649,61 USD totaal voor 3 nachten

8–11 nov 2026

$ 4.383,36 USD totaal voor 30 nachten

8 nov – 8 dec 2026

$ 655,96 USD totaal voor 4 nachten

8–12 nov 2026

$ 577,42 USD totaal voor 4 nachten

8–12 nov 2026

$ 4.424,90 USD totaal voor 30 nachten

8 nov – 8 dec 2026

Waarom Chicago bezoeken

Ontdek wat Chicago een perfecte bestemming voor vakantieverhuur maakt.

Theater & Comedy Scène

Wereldberoemd om zijn levendige uitvoeringen.

Bekijk een show in het iconische Chicago Theatre of lach de nacht weg bij The Second City, beide gelegen op minder dan een mijl van het centrum.

Magnificent Mile

Shop iconische merken op Michigan Avenue.

Deze beroemde straat herbergt meer dan 460 winkels, waaronder high-end boetieks en flagship stores, op slechts 10 minuten lopen van Millennium Park.

Deep-Dish Delicatessen

Geniet van de pizza-erfgoed van Chicago.

Probeer een pizza bij Lou Malnati's of Giordano's, vaste waarden voor liefhebbers van deep-dish, beide gemakkelijk bereikbaar vanuit de Loop.

Art Institute of Chicago

Thuisbasis van duizenden kunstwerken.

Gelegen in Grant Park, dit museum heeft stukken van Impressionistische meesters. Het is slechts een korte wandeling van het stadscentrum.

Waar te verblijven in Chicago

De beste gebieden en buurten voor uw vakantieverhuur in Chicago.

De Loop

De thuisbasis van de iconische architectuur van Chicago en het zakelijke district, met een levendige kunstscene en groene ruimtes zoals Millennium Park.

Het beste voor: zakelijke reizigers, architectuurliefhebbers, eerste bezoekers

Wicker Park

Bekend om de levendige straatkunst en eclectische muziekpodia, een toevluchtsoord voor creatieve geesten en foodies, met unieke eet- en winkelmogelijkheden.

Het beste voor: jonge reizigers, muzikanten, kunstenaars

Lincoln Park

Bevat een groot groen gebied met de gratis toegankelijke Lincoln Park Zoo, samen met verschillende culturele instellingen en gezinsvriendelijke activiteiten.

Het beste voor: gezinnen, natuurliefhebbers, dierentuinliefhebbers

Hyde Park

Een cultureel centrum met de Universiteit van Chicago en het Museum of Science and Industry, rijk aan geschiedenis en academische prestige.

Het beste voor: geschiedenisfanaten, academici, museumbezoekers

Vind Chicago vakantieverhuur die bij uw stijl passen

Apartments, vacation homes, condos en meer — kies het type Chicago vakantieverhuur dat u wilt, en boek het direct bij de host.

Chicago vakantieverhuur met free WiFi, hot tub of air conditioning

Free WiFi, hot tub, air conditioning en meer — elke Chicago vakantieverhuur hier is vermeld door een geverifieerde host en direct boekbaar, met de prijs die de host heeft ingesteld.

Topattracties in Chicago

Allemaal binnen rijafstand van vakantieverhuur in Chicago.

The Art Institute of Chicago

Houses over 300,000 artworks, from ancient to modern. · 0.5 miles

Lincoln Park Zoo

Free-entry zoo with diverse animal exhibits and conservation programs. · 3 miles

Chicago Symphony Orchestra

World-class performances in a renowned venue. · 0.4 miles

Magnificent Mile

Premier shopping district with hundreds of stores. · 1 mile

Millennium Park

Famous for Cloud Gate, it's a center for music and art. · 0.2 miles

The Field Museum

Natural history museum featuring the famous T. rex, Sue. · 1.2 miles

Beste tijd om Chicago te bezoeken

Best months to visit are May, June, and September with mild temperatures (60s-70s °F) and comfortable weather.

Voor lagere prijzen en minder drukte is van November tot Maart de beste tijd om te boeken.

Beste waardeNov – Maa

NovNu

48°F9°C

Neerslag Gemiddeld

Vraag Laag

Dec

36°F2°C

Neerslag Gemiddeld

Vraag Laag

Jan

31°F-1°C

Neerslag Gemiddeld

Vraag Laag

Feb

36°F2°C

Neerslag Gemiddeld

Vraag Laag

Maa

47°F8°C

Neerslag Gemiddeld

Vraag Laag

Apr

59°F15°C

Neerslag Gemiddeld

Vraag Gemiddeld

Mei

70°F21°C

Neerslag Gemiddeld

Vraag Gemiddeld

Jun

79°F26°C

Neerslag Gemiddeld

Vraag Piek

Jul

84°F29°C

Neerslag Gemiddeld

Vraag Piek

Aug

82°F28°C

Neerslag Gemiddeld

Vraag Piek

Sep

75°F24°C

Neerslag Gemiddeld

Vraag Gemiddeld

Okt

63°F17°C

Neerslag Gemiddeld

Vraag Gemiddeld

Hoe te reizen in en rond Chicago

Chicago offers extensive public transit, major airports, and bike-friendly streets for easy navigation.

Airports
O'HARE INTERNATIONAL AIRPORT
Located 17 miles northwest of downtown, offering global connections.
MIDWAY INTERNATIONAL AIRPORT
Located 10 miles southwest of downtown, convenient for domestic flights.
Public Transit
CHICAGO 'L' TRAINS
Run by the CTA, providing access across the city and suburbs.
CTA BUS SERVICE
Extensive network serving all major neighborhoods and attractions.
Biking
DIVVY BIKE SHARE
Available citywide with numerous stations, convenient for short trips.

Vergelijkbare vakantieverhuur in de buurt van Chicago

Huizen binnen 60 mijl van Chicago, van geverifieerde hosts.

Stunning Lake house on peaceful Sta

5 bd·2½ ba
4.86· 22

$ 2.256,65 USD totaal voor 5 nachten

8–13 nov 2026

*King bed *Outdoor Living *Sought-After Area

3 bd·1½ ba
5· 135

$ 1.492,00 USD totaal voor 3 nachten

19–22 nov 2026

Single-Family Home. Fully Furnished

3 bd·2 ba
5· 16

$ 1.935,00 USD totaal voor 6 nachten

8–14 nov 2026

Cute 2 br with King and Queen

2 bd·1 ba
4.95· 20

Lovely 1 bed room apartment, all to yourself.

1 bd·1 ba
4.87· 94

$ 395,90 USD totaal voor 3 nachten

16–19 nov 2026

Waterfront Cottage/sauna/kayaks/firepit/dock

1 bd·1 ba
4.88· 40

$ 795,00 USD totaal voor 3 nachten

8–11 nov 2026

$ 939,53 USD totaal voor 3 nachten

8–11 nov 2026

$ 1.299,48 USD totaal voor 3 nachten

8–11 nov 2026

Modern forest retreat: fast wifi, hot tub, firepit

4 bd·3 ba
5· 27

$ 2.295,00 USD totaal voor 3 nachten

8–11 nov 2026

Deer Run Log Cabin

3 bd·2 ba

$ 2.112,80 USD $ 2.007,17 USD totaal voor 3 nachten

8–11 nov 2026

Deer Run Lodge

4 bd·3 ba
5· 1

$ 3.333,31 USD $ 2.833,31 USD totaal voor 3 nachten

8–11 nov 2026

Beachfront Home with Jacuzzi & Kayaks - Premier

2 bd·1½ ba
5· 3

$ 5.426,42 USD totaal voor 30 nachten

8 nov – 8 dec 2026

Verken in de buurt van Chicago

Steden en dorpen binnen rijafstand van Chicago, elk direct boekbaar bij de host.

Waarom gasten boeken op Houfy

  • Direct met de host

    Bericht de host voordat je boekt. Stel vragen, bevestig details en handel met de persoon die de woning bezit.

  • Geverifieerde hosts

    Elke host voltooit een identiteitsverificatie voordat een advertentie live gaat.

  • Gespecificeerde prijzen

    Elke kostenpost wordt weergegeven voordat je betaalt — inclusief de API-verbinding kosten, waar van toepassing.

Veelgestelde vragen

Snelle antwoorden over het boeken van vakantieverhuur in Chicago en wat directe boekingen op Houfy eigenlijk betekenen.

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