Chicago Union Station holiday lettings
We found 3,702 holiday rentals — enter your dates for availability
Choose the perfect holiday home within easy reach of Chicago Union Station. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Chicago Union Station
Showing deals for:7 Nov - 14 Nov
Image gallery for Unbeatable Top Floor: Views, Central, Modern
1010 out of 10 rating
Exceptional
(6 reviews)
Unbeatable Top Floor: Views, Central, Modern
Chicago, IL
7% off
Price is £3,242
£3,242
£463 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
7% off
Price is £4,819
£4,819
£688 per night
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is £2,507
£2,507
£358 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is £2,851
£2,851
£407 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(41 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
7% off
Price is £2,328
£2,328
£333 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
1010 out of 10 rating
Exceptional
(32 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
8% off
Price is £3,824
£3,824
£546 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
7% off
Price is £3,314
£3,314
£473 per night
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is £4,074
£4,074
£582 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is £3,145
£3,145
£449 per night
includes taxes & fees
Image gallery for Gorgeous N. Kenwood/Hyde Park
8.08.0 out of 10 rating
Very good
(7 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is £1,654
£1,654
£236 per night
includes taxes & fees
Image gallery for Penthouse Corner 3BR in Streeterville | Roof Deck
9.49.4 out of 10 rating
Exceptional
(23 reviews)
Penthouse Corner 3BR in Streeterville | Roof Deck
Chicago, Illinois
7% off
Price is £3,022
£3,022
£432 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
7% off
Price is £3,019
£3,019
£431 per night
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
6% off
Price is £1,518
£1,518
£217 per night
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is £973
£973
£139 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is £1,380
£1,380
£197 per night
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
14% off
Price is £1,720
£1,720
£246 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(32 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
7% off
Price is £1,584
£1,584
£226 per night
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
7% off
Price is £2,626
£2,626
£375 per night
includes taxes & fees
Image gallery for Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
Worth, IL
5% off
Price is £1,447
£1,447
£207 per night
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(60 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
7% off
Price is £2,391
£2,391
£342 per night
includes taxes & fees
Image gallery for New Garden Studio near Wrigley/DePaul/Dwtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
New Garden Studio near Wrigley/DePaul/Dwtn
Chicago, IL
7% off
Price is £1,238
£1,238
£177 per night
includes taxes & fees
Image gallery for Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
Chicago, IL
13% off
Price is £3,277
£3,277
£468 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is £3,985
£3,985
£569 per night
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Experience Chicago living near United Center
Chicago, IL
7% off
Price is £1,026
£1,026
£147 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago Union Station
Gorgeous N. Kenwood/Hyde Park
Sleeps 11 · 3 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
7 reviews(7 reviews)
Cozy 2BR haus inn Pilsen with patio and fire pit 🔥
Sleeps 6 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
24 reviews(24 reviews)
Smart Simple and Spacious 4BR Apt State 203
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
91 reviews(91 reviews)
Home away from home. Family-oriented neighborhood.
Sleeps 6 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
23 reviews(23 reviews)
Luxurious 3 Bedroom Apartment in Chicago
Sleeps 5 · 3 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
16 reviews(16 reviews)
Top rated rentals - Chicago Union Station
Fabulous
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value