Holiday apartment in Chicago
Find the perfect holiday apartment or ideal holiday house in Chicago (United States) – with more space, a private kitchen, and full privacy.
Where can I find a good holiday rental in Chicago?
Our partner FeWo-direkt lists apartments, villas and holiday homes in Chicago with photos, guest reviews and live availability.
Holiday apartments in Chicago
Browse thousands of holiday apartments and holiday homes on FeWo-direkt – with guest reviews, photos, and flexible cancellation policies.
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How much does a holiday to Chicago cost?
Currently, offers for Chicago start at 1,922 €. The average offer price is around 3,388 € (41 accommodations in comparison, as of 15 October 2026).
Live data from our offer comparison — updated daily.
1,922 €
Offers from
41
Properties compared
96 %
Ø Recommendation (35 hotels)
December
Cheapest travel month currently
Which accommodations in Chicago are the best rated?
The best-rated options in our offer comparison for Chicago currently are Hotel Riu Plaza Chicago (100 % recommendation), Warwick Allerton Hotel Chicago (99 % recommendation) and Sofitel Chicago Magnificent Mile (100 % recommendation). This is based on guest reviews from travel providers (only properties with at least 25 reviews).
Hotel Riu Plaza Chicago
100 % recommendation (141)
from 3,678 € (7 days)
Warwick Allerton Hotel Chicago ★★★★
99 % recommendation (78)
from 1,922 € (7 days)
Sofitel Chicago Magnificent Mile ★★★★★
100 % recommendation (71)
from 4,067 € (7 days)
When is the best time to visit Chicago?
The best time to visit Chicago is May–September (warm summer, festivals), September–October (autumn). In summer: Warm, 25–32 °C, sunny with occasional thunderstorms. In winter: Very cold, -10–-1 °C, icy wind from Lake Michigan.
Best travel time
May–September (warm summer, festivals), September–October (autumn)
Summer
Warm, 25–32 °C, sunny with occasional thunderstorms
Winter
Very cold, -10–-1 °C, icy wind from Lake Michigan
Highlights
Fascinating culture
Is a holiday rental in Chicago worth it?
A holiday apartment in Chicago offers you the perfect combination of independence and comfort. Enjoy Fascinating culture and experience Chicago like a local – with your own retreat after an action-packed day.
Chicago is America's third-largest city and an architectural masterpiece on the shores of Lake Michigan. The Windy City, as it is affectionately called, captivates with a unique skyline, a vibrant cultural scene, and a culinary diversity that is unparalleled. Here, the skyscraper was invented, and to this day, the architecture is among the most impressive in the world.
Millennium Park with the iconic Cloud Gate — better known as The Bean — is the heart of the city. The Magnificent Mile offers world-class shopping, while the Art Institute of Chicago houses one of the most significant art collections in the world. A boat tour on the Chicago River reveals the architectural treasures of the city from a unique perspective. Wicker Park and Logan Square are the trendy neighborhoods with independent boutiques and hip cafes.
Culinarily, Chicago is heavyweight: Deep-Dish Pizza, Chicago-Style Hot Dogs, and a growing number of star-rated restaurants make the city a gourmet paradise. The blues and jazz scene in clubs like Kingston Mines is legendary. In summer, the 42 km of lakeshore transform into beaches reminiscent of a seaside coast. With top-notch museums, lively neighborhoods, and the warmth of the Midwest, Chicago is a world city with soul.
What are the highlights of Chicago?
The iconic park with the reflective Bean sculpture, the Jay Pritzker Pavilion, and the Crown Fountain.
The famous boat ride on the Chicago River showcases the history of skyscrapers – the best city tour in the USA.
One of the oldest and largest art museums in the USA with works by Monet, Renoir, and Grant Wood's American Gothic.
Chicago's popular amusement pier on Lake Michigan with a Ferris wheel, restaurants, and fireworks in summer.
Chicago is the blues capital of the world – live music in clubs like Buddy Guy’s Legends and Kingston Mines.
When is Chicago the cheapest?
Based on current offer prices, December is currently the cheapest travel month for Chicago.
How well are the hotels in Chicago rated?
The 35 rated accommodations in Chicago have an average recommendation of 96 %.
What should I look out for when renting in Chicago?
The best time to visit Chicago is May–September (warm summer, festivals), September–October (autumn). For the cheapest holiday apartments, we recommend booking early – especially in peak season, popular accommodations get booked up quickly. Pay attention to reviews from previous guests and check if final cleaning and bed linen are included in the price.
Is a holiday rental worth it for a longer stay?
Holiday apartments are particularly suitable for longer stays: From a week onwards, the price per night often drops significantly. Use the private kitchen to save money, and enjoy the freedom to shape your day at your own pace – without fixed meal times or hotel rules.
Which tools help you plan your Chicago holiday?
4 free tools help you plan your trip to Chicago: Holiday finder, Budget calculator, Packing list and CO₂ calculator. They work directly in your browser.
Where else are there holiday rentals in the United States?
Besides Chicago, there are more holiday rentals destinations in the United States with their own page and price comparison: New York, New York City, Miami and Los Angeles and 2 more.
