Vacation Rentals in Chicago, United States from 29$/Night

Chicago boasts attractions like Millennium Park, Navy Pier, and the Art Institute of Chicago. You can also catch a game at Wrigley Field or enjoy the waterfront at Oak Street Beach. Many options await you, from boutique hotels in the West Loop to hotels with pools and pet-friendly hotels scattered throughout the city. This selection includes the best Marriott Hotels, Wyndham Hotels, and IHG Hotels for fantastic stays. Book early, especially during festivals, and use the Blue Line train to navigate easily.

101-120 out of 214

Sort by:

Price: low to high
Price: high to low
Guest rating: high to low
Popularity: high to low

3 Bed 2 Bath Chicago Retreat W Balcony & Parking Apartment

Map2.4 mi from City Centre

Select

Walk To Metra Long-Term Getaway In Chicago! Apartment

Map8.5 mi from City Centre

Select

2Br Apt Beautifully Furnished - Grace 11-1

Map5.2 mi from City Centre400 yd from Wrigley Field

Select

Cozy 1 Bed By The Lake Park

Map9.9 mi from City Centre

Select

Charming Lakefront Stunning View North Chicago

Map9.9 mi from City Centre

Select

Dwntn 10Mins And Sleeps 10 In Vintage And Free Parking

Map2.8 mi from City Centre1.1 mi from United Center

Select

1Br City Loft With Modern Glass Views

Map4.3 mi from City Centre

FromUS$ 486 /nightSelect

Comfy Garden Suite In Andersonville

Map7.2 mi from City Centre600 yd from Berwyn

Select

Spacious Three Bedroom Apt With Parking And Patio

Map5.4 mi from City Centre600 yd from Logan Square

Select

Harmony Near The Lake, Modern 3 Bed 2 Bath

Map8.0 mi from City Centre700 yd from University of Chicago Dental

Select

Luxurious Lincoln Park Home With Gourmet Kitchen

Map3.7 mi from City Centre900 yd from Diversey

FromUS$ 524 /nightSelect

Explore The City Sleek 2Br Gem In North Chicago

Map4.0 mi from City Centre1000 yd from California Station (Blue Line)

Select

Amazing Location 3Br Gem In Logan Square W Parking

Map4.0 mi from City Centre1000 yd from California Station (Blue Line)

Select

Modern 6Br House Steps To Wrigleyville

Map5.3 mi from City Centre700 yd from Wrigley Field

Select

Chic 2Br Getaway Queen Beds Fast Wifi

Map8.8 mi from City Centre300 yd from Hoyne Avenue Fields

Select

Comfy & Central 1Br Steps From Loyola & Dining

Map8.8 mi from City Centre300 yd from Hoyne Avenue Fields

Select

Affordable Private Room 2 - Shared

Map3.6 mi from City Centre700 yd from Indiana

FromUS$ 284 /nightSelect

Affordable Private Room 2 - Shared

Map3.6 mi from City Centre700 yd from Indiana

Select

Affordable Private Room - Shared

Map3.6 mi from City Centre700 yd from Indiana

Select

The Best View In America

Map1.3 mi from City Centre800 yd from Millennium Park

Select

Flexible Price Range for Vacation Homes in Chicago

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price

US$ 2 453

⬇️ The lowest price

US$ 29

💸 Average price for

4-star hotels

US$ 279

Apartments

US$ 306

Top vacation homes in Chicago

Based on guest reviews from the past 12 months

Vibrant Wrigleyville Escapes:

Charming Boutique Abodes:

Luxery Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena

Cultural Hotspots in Little Italy:

Convenient Airport Access:

Days Inn Melrose Park/O'Hare South

Homey Retreats in the City:

5430 Happy Home

Urban Living with Style:

How to get to Chicago

Explore local transportation options with ease

Airports

Chicago O'Hare International (ORD)

Midway International (MDW)

FAQs about Chicago rentals

Get answers to common questions and plan your adventure smoothly

Which vacation rentals in Chicago are best for families with children?

Properties like 'Wrigley Oasis! Steps From The Field! - 3Bd 1Ba' and 'Wrigleyville Friends Unit - 5Bdrm' are spacious and family-friendly with amenities to accommodate larger groups.

What vacation rentals offer unique views in Chicago?

'Modern 2Br Loft With Amazing City Skyline View And Optional Parking' provides a striking skyline view, while 'Fulbrix Bright Designer Apartments With West Loop Views' offers an impressive perspective of the urban landscape.

Which vacation rentals in Chicago are located close to major attractions?

The 'Double Play Wrigley - Prime Location! - 1 Min Walk To Wrigley Field' is conveniently located near Wrigley Field. Similarly, 'Chicago 2Br Suite Perfect For Convention And Business Trips' is near McCormick Place and other central attractions.

What are the cheapest vacation rental options in Chicago?

Affordable choices include properties like 'Cozy 1 Bedroom, 1 Min From Irving Park Blue Line, Free Parking' and 'Convenient & Newly Decorated 1Br Apartment - Roscoe 1D', which typically range from $80 to $120 per night.

Are there any vacation rentals in Chicago suited for couples looking for a romantic getaway?

Consider 'Chic Retreat | Fully Equipped Cozy 4/5 Br' or 'Stunning Duplex Condo #1 - Downtown River North' for a cozy yet upscale romantic experience, offering privacy and stylish design.

Vacation Rentals Insights in Chicago

This guide evaluates various vacation rentals in Chicago, reviewing 7 properties to provide crucial information for your travel planning, including pricing, local fees, and prime locations.

Typical nightly rates range from $100 to $300 USD.

Peak seasons include summer (June to August) and holidays.

Local taxes and fees can add around 17% to total booking costs.

Key attractions like Millennium Park are about 1.5 miles from downtown rentals.

Book early-3 to 6 months ahead-for the best options.

Vacation rentals in Chicago, United States

Flexible Price Range for Vacation Homes in Chicago

Top vacation homes in Chicago

How to get to Chicago

FAQs about Chicago rentals

Vacation Rentals Insights in Chicago