
Midway Station holiday rentals
We found 3,712 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals near Midway Station that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Midway Station
Showing deals for:10 Oct - 17 Oct
Image gallery for Luxury Loft Collection 703 - Terrace - River North

1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$13,537
AU$13,537
AU$1,934 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment

9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is AU$11,724
AU$11,724
AU$1,675 per night
includes taxes & fees
Image gallery for #1810 - Kasa Magnificent Mile Chicago

9.29.2 out of 10 rating
Wonderful
(9 reviews)
#1810 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$6,176
AU$6,176
AU$882 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

1010 out of 10 rating
Exceptional
(31 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
9% off
Price is AU$6,997
AU$6,997
AU$1,000 per night
includes taxes & fees
Image gallery for #1402 - Kasa Magnificent Mile Chicago

9.49.4 out of 10 rating
Exceptional
(25 reviews)
#1402 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$9,609
AU$9,609
AU$1,373 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is AU$9,490
AU$9,490
AU$1,356 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North

9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
8% off
Price is AU$14,501
AU$14,501
AU$2,072 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago

9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
8% off
Price is AU$14,391
AU$14,391
AU$2,056 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 1

9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 1
Chicago, Illinois
15% off
Price is AU$6,516
AU$6,516
AU$931 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!

9.89.8 out of 10 rating
Exceptional
(65 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is AU$3,599
AU$3,599
AU$514 per night
includes taxes & fees
Image gallery for Luxury SOHO Styled Two-Level Townhouse - Old Town

1010 out of 10 rating
Exceptional
(15 reviews)
Luxury SOHO Styled Two-Level Townhouse - Old Town
Chicago, Illinois
8% off
Price is AU$12,481
AU$12,481
AU$1,783 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve

1010 out of 10 rating
Exceptional
(18 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is AU$2,893
AU$2,893
AU$413 per night
includes taxes & fees
Image gallery for Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Oak Park, Illinois
7% off
Price is AU$3,417
AU$3,417
AU$488 per night
includes taxes & fees
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
8% off
Price is AU$14,443
AU$14,443
AU$2,063 per night
includes taxes & fees
Image gallery for The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!

9.09.0 out of 10 rating
Wonderful
(6 reviews)
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Chicago, IL
16% off
Price is AU$4,746
AU$4,746
AU$678 per night
includes taxes & fees
Image gallery for Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown

1010 out of 10 rating
Exceptional
(5 reviews)
Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
Chicago, IL
11% off
Price is AU$5,808
AU$5,808
AU$830 per night
includes taxes & fees
Image gallery for Spacious 5-Bedroom Retreat in Forest Park

9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious 5-Bedroom Retreat in Forest Park
Forest Park, IL
34% off
Price is AU$6,981
AU$6,981
AU$997 per night
includes taxes & fees
Image gallery for NEW Contemporary Home - 5BR/3.5BA+office+garage

9.29.2 out of 10 rating
Wonderful
(12 reviews)
NEW Contemporary Home - 5BR/3.5BA+office+garage
Chicago, IL
7% off
Price is AU$9,647
AU$9,647
AU$1,378 per night
includes taxes & fees
Image gallery for Stunning & Spacious 7BD Home with garage!

8.48.4 out of 10 rating
Very good
(5 reviews)
Stunning & Spacious 7BD Home with garage!
Chicago, IL
7% off
Price is AU$12,684
AU$12,684
AU$1,812 per night
includes taxes & fees
Image gallery for PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

9.69.6 out of 10 rating
Exceptional
(10 reviews)
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard, IL
8% off
Price is AU$3,874
AU$3,874
AU$553 per night
includes taxes & fees
Image gallery for Cozy 2BR/1BA Garden Apartment Near Lincoln Square

8.28.2 out of 10 rating
Very good
(10 reviews)
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Chicago, IL
6% off
Price is AU$2,872
AU$2,872
AU$410 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Chicago, IL
7% off
Price is AU$4,198
AU$4,198
AU$600 per night
includes taxes & fees
Image gallery for Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib
Chicago, IL
19% off
Price is AU$4,357
AU$4,357
AU$622 per night
includes taxes & fees
Image gallery for Oak Park, IL, entire house, short walk to train.

9.49.4 out of 10 rating
Exceptional
(20 reviews)
Oak Park, IL, entire house, short walk to train.
Oak Park, IL
8% off
Price is AU$4,601
AU$4,601
AU$657 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Midway Station
Charming 2-bedroom residence in Jefferson Park, Chicago!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Relax in style: Chic 2 bedroom haven in brickell.
Sleeps 4 · 2 bedrooms · 1 bathroom
3.03.0 out of 10
2 reviews(2 reviews)
Country White House
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Dog-Friendly Blue Island Apt w/ Backyard!
Sleeps 7 · 3 bedrooms · 1 bathroom
5.65.6 out of 10
4 reviews(4 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, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value