Have you been daydreaming about romantic weekend getaways in Illinois?

It’s time to forget about fantasies and get to planning! From fine dining in downtown Chi-town to lounging away the morning at a quiet little bed and breakfast, there is plenty to do for two in Illinois. Our list of the top romantic weekend getaways in Illinois gives you plenty of ideas for a quick trip. For even more great ideas, check out our recent article on weekend getaways in the U.S..

1. Visit the Windy City

weekend getaways in Illinois - Windy City

The Windy City itself is one of the most exciting weekend getaways in Illinois. Poised on the edge of Lake Michigan, Chicago is full of beaches and parks to explore with your lover. There is a total of 570 parks in Chicago, with the 1200-acre Lincoln Park being the largest and most impressive. The Windy City has pro sports teams including NBA, NFL, and NHL if you and the boo are into sports events. Chi-town is also ripe with nightclubs and comedy bars, so a night on the town is always an exciting option. If Art is a shared passion, consider visiting the Art Institute of Chicago to view one of the most significant collections of American art in the entire country.

2. Hit Up The Waterfalls at Starved Rock State Park

If you’re into the great outdoors, a weekend getaway in Illinois will satisfy the nature lover inside of you. The Starved Rock State Park National landmark is around an hour and a half away from Chicago. It is teeming with canyons, rolling green hills, and beautiful landscape. There are over a dozen waterfalls available for you and your loved one to explore by yourselves or via a guided hike. The park has a campground, picnicking area with tables and shelters, restrooms, a guest lodge and a small camp store for all your overnight camping needs. For an even more enjoyable experience, consider visiting the Starved Rock State Park in the winter time when you’ll be able to view thousands of bald eagles.

3. Stay Over at the Victorian Rose Garden Bed and Breakfast

weekend getaways in Illinois - Victorian Rose Garden Bed

The Victorian Rose Garden Bed and Breakfast is a surefire weekend getaway that’s sure to rekindle the passion between you and your significant other. This old Victorian home was built back in 1886 as a wedding present to James and Emma Harvey. The house changed owners in 1916 and again in the early 1970’s. The home has been operating as a historic bed and breakfast since 1995. Come to enjoy a lazy day with plenty of contemporary amenities and a fabulous full breakfast from Sherry Brewer (the homeowner).

4. Have Dinner with Your Boo at Francesca’s Fortunato

When it comes to a romantic dinner for two, there are few places with as much atmosphere in Illinois than Francesca’s Fortunato. Your lover will surely be impressed by the coziness of the site. The restaurant has a beautiful bar, a lovely fireplace, and serve some of the most exquisite food in the entire state. Service is top-notch, the drinks are amazing, and the plate arrangements are to die for. If you love Italian cuisine, Francesca’s Fortunato might just become your new go-to food place for you and your boo.

5. Check out the Windy City’s Skyline from Promontory Point

weekend getaways in Illinois - Promontory Point

One of the most picturesque views of the Windy City skyline is from Promontory Point in Hyde Park. As far as quick and affordable weekend getaways in Illinois go, a day trip to the Lakefront Trail at Promontory Park is hard to beat. You can take a stroll along the water, enjoy the distant view of Chicago, and have a nice picnic together in Hyde Park before heading back home.

6. Visit Illinois’ Second Largest City

The second largest city in the state of Illinois sits just outside of Chicago. Known as “the Forest City” for its 20,000 plus acres of greenery, Rockford is home to four rivers, Rock Cut State Park, golf courses, hiking trails and a Midway Village, a fully preserved pioneer village. For couples who enjoy reminiscing over eras gone by, and steeping in regional history, Rockford, Illinois is an excellent weekend getaway waiting to happen. For the nature-loving couple, do yourselves a favor when you’re in Rockford by checking out the Legendary Anderson Gardens.

7. Explore Bloomington’s Park System

weekend getaways in Illinois - Bloomington’s Park System

For the outdoorsy couple, Illinois’ 12th largest city is well worth the visit. If you and your partner like strolling through gardens and tree groves in city parks as well as along sprawling waterfronts, then exploring Bloomington’s extensive park system might be for you. There is a total of 44 parks in the Bloomington area as well as three golf courses, a zoo, a theater, a symphony, and even a ballet corps. For the outgoing couple, Bloomington is also home to a massive indoor rock climbing park.

8. Rent a Room at The Inn at Irish Hollow

An alternative to the Sherry Brewer’s Victorian Bed and Breakfast is renting a room for the weekend at The Inn at Irish Hollow. It doesn’t get much more romantic than this fairytale-like cottage planted firmly in the middle of 500 acres of farmland. The Inn itself draws inspiration from bygone days with its stone fireplaces and claw-foot tubs. If you want to spice things up, the Inn at Irish Hollow also offers whirlpools, massages, as well as breakfast served straight to your room.

9. Attend the Chicago Symphony Orchestra

weekend getaways in Illinois - Chicago Symphony Orchestra

Started in the late 19th century, the Chicago Symphony Orchestra is considered one of the most excellent anywhere. The Chicago Symphony Orchestra performs more than a hundred concerts a year. So the chances are, you won’t have a hard time finding one that fits your timeline. The Symphony Center is easily located on the North Shore of Chicago. If music is your thing, the CSO makes for an extremely enchanting evening.

10. Take a Trip to Evanston and See the Lighthouse

Another cozy little town to visit for the weekend is Evanston, Illinois. This charming little suburb is tucked away just to the North of Chi-town. It is home to multiple restaurants ideal for couples, plentiful music venues, and several interesting historical sites. The Grosse Point Lighthouse is one such historical attraction. After a number of shipwrecks during the 19th century, the lighthouse was put in its current location back in 1873. While working, the Lighthouse was the brightest light in the region.

11. Jump on the Mississippi Valley Wine Trail

weekend getaways in Illinois - Mississippi Valley Wine Trail

Quincy, Illinois, while probably not one of the first locations that would come to mind while planning weekend getaways in Illinois, is quite the little gem for couples seeking a romantic atmosphere. The quaint German-style town sits overlooking the mighty Mississippi River. In the past, Quincy was a sanctuary for Mormons fleeing the eastern side of Missouri and seeking the safety of Illinois. It was also an important station along the Underground Railroad. One of the most unique weekend getaway opportunities in Illinois is to experience the Mississippi Valley Wine Trail. Situated along the western border of Illinois and the Mississippi River, the trail is made up of several local family-owned and operated wineries. From first generation to fifth generation winemakers, the Mississippi Valley Wine Trail offers access to the some of the finest hand-crafted wine in the area. For couples looking for a romantic weekend in Illinois, there are few getaway destinations as authentic and rewarding as partaking in the Mississippi Valley Wine Trail.

12. Take a Hike and Grab a Coffee at The Morton Arboretum

The Morton Arboretum in Lisle, Illinois sits just outside of Chicago and consists of 1700 plus acres of nature. There are bike paths, walking trails, gardens, and even a maze at the arboretum. For those who enjoy both nature and literature, the Sterling Morton Library has nearly 30,000 works on botany, trees, and nature in general. The Morton Arboretum also has a gift shop and cafe, so you can enjoy a cup of joe with your partner before, during, or after wandering from garden to garden.

13. Visit the Shawnee National Forest Garden of the Gods

weekend getaways in Illinois - Shawnee National Forest

Illinois is home to several state and national parks, including the Shawnee National Forest in the southern part of the state. The 268,000-acre park sits nestled into Shawnee Hills and the ridges of the Ozarks, a lush green wilderness of forests and wetlands dotted with cypress trees and wildflowers. The Garden of the Gods is one of the most breathtaking natural landscapes to be found in Illinois. Rock formations such as the Devil’s Smoke Stack and Anvil Rock are among t ourists favorites. Cabins, as well as campgrounds, are available also, making a trip to the Shawnee National Forest a fun and exciting weekend getaway in Illinois. For the couple who doesn’t feel right leaving their dog at home while they get away for the weekend, the trails at the Shawnee National Forest welcome dogs as long as you bring their leash!

14. Check Out the Fabyan Forest Preserve and Windmill

As far as Forests go, the Fabyan Forest Preserve, located in Northern Illinois, is one of the most beautiful pieces of protected nature worthy checking out in the whole state. Colonel Fabyan acquired this massive piece of land in the late 1800’s, today it is known as the Fabyan estate. The estate sits on the banks of the Fox River. Nature-loving couples will enjoy the sprawling Fox River Trail. Fabyan had a massive five-story Dutch windmill installed on the property in the 1920’s. The mill, already 70 years old when Fabyan moved it to his estate, is a favorite attraction of tourists to the Preserve.

15. Visit the Cahokia World Heritage Site

weekend getaways in Illinois - Cahokia World Heritage Site

For the couple that genuinely appreciates history, there are few sites in the state of Illinois more intriguing than the Cahokia World Heritage Site. Once the largest city in North America, this pre-Columbian Native American site was home to the ancient Mississippian people. The city had one of the most massive pyramids on Earth, as well as hundreds of small temples surrounding the pyramid. There is a museum for those interested in exploring the scholarly side of Cahokia history, as well as walking trails, a gift shop, and a life-size replica village.

16. The Garden of the Phoenix in Jackson Park

Another fantastic outdoor weekend getaway in Illinois is a visit to the Garden of the Phoenix in Jackson Park. This 600-acre park has basketball and tennis courts, a baseball field, golf course, playground and trails for hiking, biking, and jogging. The site is famous for being the location of the World’s Columbian Exposition way back in 1893. The Garden of the Phoenix makes for an excellent picnic date or just a nice place to stop and talk a stroll as part of your overall weekend getaway in Illinois.

17. Attend Adler After Dark

weekend getaways in Illinois - Adler After Dark

For an occasion you and your sweetheart won’t soon forget, visiting the Adler Planetarium will give you a better view of the stars than practically anywhere else east of the Mississippi River. The Planetarium was first constructed back in 1930 making it a National Landmark as the oldest Planetarium in North America. An unobstructed view of Chicago’s skyline is visible from the Adler. Once a month, the museum hosts their “Adler After Dark” 21 and over series. The events are centered around learning about the night sky, and of course, there is also beer, wine, and food to look forward to. There are few one of a kind weekend getaways in Illinois that compare for sweethearts of the stars.

18. See a Movie at the Chicago Theatre

For couples who love the more refined things in life, the 5,000 seat Chicago Theatre is a superb venue to attend while on weekend getaways in Illinois. Open in 1921, this baroque-style movie theatre is as lovely as it ever was. There are few cinemas in the country with this comfortable of an atmosphere. As part of your overall weekend getaway, this Chicago Theatre makes a great stopping point.

19. Visit the Lincoln Park (Alfred Caldwell) Lily Pool

weekend getaways in Illinois - Lily Pool

One of the most well-hidden treasures of the Windy City’s park system is the “Alfred Caldwell” Lily Pool in Lincoln Park. Caldwell developed the pool back in the early 20th century. Today, it is accessible from spring until fall each year. The Lincoln Park lily pool has become a hotspot for couples popping the question due to its natural romantic vibe. It is also commonly used for couples holding small weddings as well. The lily pool is a must-do for love-birds on weekend getaways in Illinois.

20. Take a Chicago Sunset Cruise

When you think of a weekend getaways in Illinois, a cruise is probably the furthest thing from your mind. If you’ve spent much time in the Great Lakes region, however, you would know better. For couples planning romantic getaways in Illinois, a Chicago Sunset Cruise is a unique way to spend an evening together in the Windy City. The cruise takes place on Lake Michigan as the sun sets on the Chicago skyline. You and your sweetheart can kick back, have a drink, and unwind before heading back to the hotel for the night.

21. Stargaze at the Garfield Park Conservatory

weekend getaways in Illinois - Garfield Park Conservatory

If you don’t have a chance to stop by the Adler Planetarium, consider visiting the Garfield Park Conservatory instead. When this one-of-a-kind park opened back in 1908, it was thought to be revolutionary. The conservatory consists of many impressive features such as the Desert House or the Fern Room and its prairie waterfall. The Garfield Park Conservatory is a great environment to stroll through holding hands with your partner just enjoying yourselves.

Making the Most of Your Romantic Weekend Getaways in Illinois

Enter your text here…It's no hard task to organize awesome romantic weekend getaways in Illinois. The most difficult part is having so many great locations and activities to plan around. From hidden glens in forested parks to sunset cruises, there are many excellent weekend getaways in Illinois for couples. The prairie state is full of historic Inns, bed and breakfasts, Italian fine-dining restaurants. It also has plenty of parks, preservations, scenic nature trails, and much more. So, what are you waiting for? Start planning your next romantic getaways in Illinois!

If you're planning a weekend getaway in the near future an don't know which bags to pack, be sure to check out our article on tote bags for weekend getaways.

Related Article: ​20 Weekend Getaways from DC (Within Driving Distance)​​​