Search Romantic Hotels in Oak Park

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oak Park Romantic Hotels

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Oak Park Romantic Hotels

Exterior detail
Carleton of Oak Park

Carleton of Oak Park

3.0 star property
Oak Park
9.2 out of 10, Wonderful, (1023)
"Spacious room, quiet night's sleep in a very pleasant historic hotel."
United States
Edward
Carleton of Oak Park
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (119)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
United States
Bethany
The price is 6.090.315 ₫
6.758.931 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Harvey House Bed & Breakfast
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2092)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3421)
"Great stay!"
United States
Rose
The price is 2.196.538 ₫
2.578.517 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
American cuisine, al fresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1922)
"Awesome staff and great location "
United States
Luis C
The price is 2.196.538 ₫
3.197.658 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Godfrey Hotel Chicago
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2984)
"Great stay"
Canada
Lorrington Ashford
The price is 1.924.909 ₫
3.033.463 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
Lobby
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5342)
"Great location "
United States
Louis
The price is 2.486.597 ₫
2.919.016 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Embassy Suites by Hilton Chicago Downtown River North
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2959)
"Great location, the staff was friendly and the room was very clean. "
United States
Breanna
The price is 2.267.734 ₫
2.662.093 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile
Exterior
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3097)
"Great stay Great staff Would love to stay again when I come back"
United States
Stephanie A
The price is 3.005.610 ₫
4.371.964 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
The Royal Sonesta Chicago Downtown
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3030)
"Beautiful hotel, very well situated near restaurants shopping and mass transit "
United States
Joan
The price is 1.793.092 ₫
2.878.967 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Warwick Allerton - Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Oak Park Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Oak Park?
Are you looking for a romantic holiday? Our guests also love Oak Park for its array of dining options and major shopping area. You might consider checking out some of the nearby sights and attractions such as Ernest Hemingway Museum and House, Frank Lloyd Wright Historic District or Madison Street Theatre. If you'd like to stay close to a certain attraction, you can sort properties by neighbourhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Oak Park?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Oak Park: The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Oak Park is 1207 mm.
What is there to do in Oak Park?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Oak Park. Couples looking for a little of everything will enjoy Oak Park for its restaurants, cafes and shopping. You might think about stopping by Ernest Hemingway Museum and House, Frank Lloyd Wright Historic District or Madison Street Theatre while you're seeing the sights.
What's the best way to get to Oak Park and around town during my romantic getaway?
These transportation options in Oak Park might help your romantic trip go off without a hitch: The closest major airport is in Chicago Midway Airport (MDW), located 7 mi (11.3 km) from the city centre. Walk to nearby metro stations such as Ridgeland Station (Green Line), Oak Park Station (Green Line) and Oak Park Station (Blue Line). If you want to explore the larger area, hop on a train at Oak Park Station.