From the Shawnee Hills Wine Trail tour in Makanda to the cool party boats in Chicago, Illinois is the ideal destination when it comes to opportunities to celebrate. Enjoy a phenomenal bachelor party in one of numerous exciting cities and towns in Illinois. Whether paddling down the Galena River or skydiving, you and the guys can bond at your own pace. From rustic cabin hideaways to luxurious downtown condos, there are plenty of Illinois vacation rentals to choose from. Check out the top bachelor party destinations in Illinois.

1. Chicago

City skyline at night.

Celebrate your epic bachelor party bash in the biggest city in Illinois, and rock out on a party boat or step out above the town into the all-glass Ledge. The Island Party boat takes your crew on cruises along the Chicago River and Lake Michigan lake front. Your party boat features a water slide and bar service, with food and beverage packages available for your group to enjoy a late morning or early afternoon. Double-dog-dare your pals to step into the Ledge on the 103rd floor of Willis Tower, the tallest building in the Western hemisphere. As you look through the glass floor, you’re 1,353 feet from the street. Afterwards, retreat to the 99th floor where you reserved a spot for the party to continue with food and beverages.

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2. Rockford

Pristine golf course.
Source: Facebook/Golf – Rockford Park District

Rockford’s vacation rentals come with great views and enough space for your group to enjoy outdoor activities or kick back indoors. Celebrate a single day of golf at one of Rockford’s five courses, including the Sinnissippi, which opened in 1912. The hills of this nine-hole, par 37 course often challenges golfers. Check with the District Bar and Grill to see if there’s a pub crawl, or go it on your own to any of the dozen or so bars in town, including Scoreboard Lounge, Kryptonite, or Rockford Billiard Cafe.

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3. Ottawa

A man diving out of a plane with a coach.
Source: skydivechicago.com/SkyDiveChicago

Take your bachelor party to new heights in Ottawa when you all suit up and go skydiving at Skydive Chicago. It’s the place to take your buddies for an adrenaline-rushing, heart-pounding, free-falling adventure like no other. For a few extra dollars, the on-site photographers, Skycam Productions, take photographs and make a video of the experience and professionally edit it to look like a movie. Get the souvenir tee-shirt while you’re there to remember this great bonding experience. You can score some lunch in the cafe inside the hangar before moving on. After skydiving, the facility features other activities, including horseback riding, wake boarding, and sand volleyball. You can score some lunch in the cafe inside the hangar.

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4. Galena

Tasting glasses lining a bar.
Source: Facebook/VisitGalena.org

Spend your bachelor party days paddling down the Galena River, also known as the Fever River. Rent kayaks, paddle boards or canoes from Fever River Outfitters, or pick up some of their bikes to see the sights on the biking trails around town. For a different type of tour, mosey over to Blaum Brothers Distilling Company of Galena. They show you how they make the spirits before serving cocktails in the copper and leather tasting room. Bring out the groom’s inner gangster by reserving Al Capone’s booth at the Log Cabin Steakhouse for some fine cocktails and food. Sound ultra-suave when you order the flaming Saganaki, a Greek appetizer of fried cheese, ignited in brandy at your table.

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5. Joliet

A Nascar car on the racetrack.
Source: nascarracingexperience.com/Nascar Racing Experience

Your Joliet vacation rental gives you easy access to Chicagoland Speedway, where your bachelor party gets the real G-force experience that lets you unleash your wildest dreams. NASCAR crew members instruct you and suit you up for driving race cars driven by Dale Earnhardt Jr., Jeff Gordon, and other NASCAR pros. Just give it the gas and stay focused for the number of laps your experience includes. You really race, pass other cars, and run your car at top speeds for the adrenaline rush of a lifetime. Continue your lucky streak at the Hollywood Casino with a buffet lunch; and, then check out the slot machines and gaming tables. Check out the bars, such as West Side Tap, the Hangover Bar, and the Sheer Bar where drinks and bar food round out the evening.

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6. Arlington Heights

Jockeys and horses at a race.
Source: Flickr/Paul Kehrer

Arlington Park makes an ideal spot for a bachelor party, where you can combine watching horse racing with a few friendly wagers. Enjoy lunch in the Million Dollar Room, which gives you excellent views of the track. Your personal television provides information about races, odds, scratches, and closed-circuit video of each race. Place your bets at the counters at the room entrance. Other dining options include Cafe Spiaggia, Jake Melnick’s, and River Roast & Ravinia. For an exciting challenge, head over to Laser Quest for the ultimate laser battle in a multi-level maze that includes music, lighting, and special effects. When the guys are ready for a plate of steaming hot wings and a cold beer to wash it down, stop at Gatsby’s Sports Pub.

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7. Makanda

Hot tub in the woods.
Source: Facebook/Oak Grove Cabins

Make Makanda your vacation destination for the ideal bachelor party for the outdoors-loving groom. Get the party started at Shawnee Bluffs Canopy Tour, which encompasses 83 acres in the Shawnee National Forest. Zoom along one of the eight zip lines at speeds up to 45 mph, zigzagging over bluffs and through the trees. Next, treat your buddies to a luxurious ride in the Gottus Limo Bus on the Shawnee Hills Wine Trail tour. Your first stop on the trail is Blue Sky Vineyard, in Makanda. In warm weather, enjoy outdoor seating on one of the terraces overlooking the vineyard. Another Makanda winery, Orlandini’s, features picnic tables where you and your buds can sit outside, drink wine, and soak up nature and fresh air.

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