Book Luxury Monthly Rentals in Chicago

We selected the 36 homes worth renting in this location

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Home spotlights in Chicago

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

All resting eyes behold a unique sanctuary blending urban spirit with an enchanting skyline whisper. The escape, nestled in the heart of Chicago's cherished West Loop, extends far beyond the eye, unfolding boundless options for dining, shopping, and entertainment.

The Skyline's Vision

The Skyline's Vision

  • 14 guests

  • 6 bedrooms

Fulton River District, Chicago

When you bring everyone to Chicago, you want a space that matches the occasion, and these skyline retreats near Fulton Market do exactly that. By day, the city is yours to explore: coffee and street art in the West Loop, vintage hunting at Randolph Street Market, picnics in Union Park, or a culinary crawl through some of the best restaurants in the Midwest.

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Step into 'The Chevelle', your unexpected sanctuary nestled amidst Chicago's lively West Loop. Previously a symbol of industrial prowess, this neighborhood is now an epicenter of world-class dining and simmering nightlife.

Artists' Rendezvous

Artists' Rendezvous

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Make a date with The Blues, a delightful haven nestled in the West Loop. This home away from home exudes an unmistakable charm, harmonising old-world coziness with a dash of modernity.


We selected the top 3% holiday homes in Chicago Monthly Rentals

Explore the 36 most perfect homes in our collection

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Most popular homes in Chicago

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

The Urban Villa

The Urban Villa

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

The Heart of the Loop

The Heart of the Loop

  • 16 guests

  • 8 bedrooms

Chicago Loop, Chicago

Metropolis Retreat

Metropolis Retreat

  • 18 guests

  • 9 bedrooms

Fulton River District, Chicago

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Chicago, Cook County, Illinois, United States, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Chicago Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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