What Are The Best Wineries in Chicago and Illinois: A Wine Lover's Guide

The Allure of Illinois Wineries

The state of Illinois, with its fertile soil and varied climate, is a fantastic region for wine production. This, coupled with Chicago's vibrant food and beverage scene, has resulted in a selection of excellent wineries to explore in both the city and the wider state.

Top Wineries in Chicago

City Winery

Situated in the vibrant West Loop neighborhood, City Winery at 1200 W Randolph St, Chicago, IL 60607, is a unique venue combining a fully functioning winery with intimate concerts, food and wine classes, and fine dining. The variety of experiences offered makes it a must-visit destination for wine and music lovers alike.

Cooper's Hawk Winery & Restaurant

Located at 58 S. Main St, Burr Ridge, IL 60527, just outside of downtown Chicago, Cooper's Hawk Winery & Restaurant boasts modern, casual dining with an impressive menu and an extensive list of wines. Each dish is created with a perfect wine pairing in mind, providing a truly immersive wine and dining experience.

Lynfred Winery

As the oldest continuously operating winery in Illinois, Lynfred Winery at 15 S Roselle Rd, Roselle, IL 60172, offers a rich history alongside its selection of quality wines. This winery has a welcoming atmosphere and hosts a variety of events and tastings that make for a memorable visit.

Top Wineries in Illinois

Illinois Sparkling Co.

Located at 106 Mill St, North Utica, IL 61373, this winery has made its mark by specializing in handcrafted, traditional-method sparkling wines. Every bottle from Illinois Sparkling Co. is crafted onsite, from pressing through fermentation, providing a local and artisanal touch.

Galena Cellars Vineyard & Winery

Nestled in the historic town of Galena at 515 S Main St, Galena, IL 61036, this winery offers over 40 different wines, from dry to sweet, red to white, and everything in between. The stunning vineyard views offer a serene backdrop for wine tastings and events.

August Hill Winery

This family-owned winery at 106 Mill St, North Utica, IL 61373, shares a tasting room with the Illinois Sparkling Co. Known for its unique, Illinois-grown wines, August Hill offers a friendly and inviting atmosphere for tasting its extensive wine list.

Blue Sky Vineyard

Situated in the heart of the Shawnee National Forest at 3150 S Rocky Comfort Rd, Makanda, IL 62958, Blue Sky Vineyard provides not just award-winning wines but a taste of Southern Illinois’ hospitality. The picturesque vineyard and Tuscan-inspired architecture make this a beautiful and tranquil place to visit.

Massbach Ridge Winery

Established in 2003, this winery located at 8837 S Massbach Rd, Elizabeth, IL 61028, prides itself on its personalized service and a diverse selection of wines. The stunning views of the rolling vineyard offer a relaxing and inviting setting for wine enthusiasts to explore their wines.

Exploring Wineries with Private Bus Rentals

Exploring different wineries in Chicago and Illinois can be a much more comfortable and safer experience with a private bus rental service. Perfect for a wide range of group sizes and uniquely catering to your transportation and travel needs, with us, you’ll be well taken care of. 

To book a private bus rental, simply provide us with your trip details and the number of passengers. Our dedication to quality, reliability, and superior customer service ensures your next wine-tasting journey is a memorable one.

Making the Most of Your Winery Visit

When visiting wineries, some tips include booking ahead, pacing your tastings, and asking plenty of questions. What can you expect? A relaxing atmosphere, knowledgeable staff, and of course, excellent wines. Always remember to take safety precautions during your visit, like drinking responsibly and ensuring a safe ride home.


Whether you're a seasoned wine connoisseur or a casual enthusiast, Chicago and Illinois offer an array of wineries to suit your palate. And with our private bus rental service, you can enjoy these experiences in style and comfort!


What are some of the best wineries in Chicago and Illinois?

City Winery, Cooper's Hawk, Lynfred Winery, Illinois Sparkling Co., and Galena Cellars Vineyard & Winery are some top choices.

How can I book a private bus rental service for a winery tour?

You can book our service by providing the details of your tour and the number of passengers.

What should I consider when visiting a winery?

Book ahead, pace your tastings, ask questions, and always drink responsibly.

Can I use a private bus rental service for any group size?

Yes, our service caters to a variety of group sizes. Just provide us with the details and we'll arrange the rest.

What types of wines are Illinois wineries known for?

Illinois wineries produce a range of wines, including Cabernet Franc, Chardonnay, and unique sparkling wines.

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Fine Rooftop Dining: Your Guide to the Best Igloos and Rooftop Bars in Chicago

While temperatures in Chicago continue to plummet, some things are really heating up in the city’s restaurant scene! They’ve been called pods, greenhouses, and igloos, to name just a few. And they’re pretty much the coolest thing about outdoor dining in Chicago. It doesn’t matter which suburb you find yourself in, there are igloos for the whole family to enjoy. Although some may require a prior reservation, this is the best option for privacy to be enjoyed with loved ones.

In this guide, we’ve put together a list of our favorites, both in and around Chicago, and hope you take full advantage of it! There’s something here for everyone! And the menu varieties are sure to impress and delight! Let’s dive right in…

14 of the best igloos in and around town


  1. London House Chicago Rooftop

Overlooking Chicago’s Magnificent Mile on the 22nd floor of the London House Chicago, you will experience lH rooftop, with breathtaking panoramic views of the city, in the comfort of cozy rooftop igloos, or dine indoors as well. Enjoy dining on the LH Rooftop, enjoying signature and classic cocktails, a large selection of craft beers and great wine, enjoy one of the best rooftop experiences in the city with great décor, cozy igloos with heaters and comfy blankets for a great night out.

  1. Winter Wonderland at the IO Godfrey

No matter how cold Chicago’s winter may be, you can enjoy a fun evening out in your cozy igloo atop the Godfrey, located at 127 West Huron.  Tucked inside your own igloo snow globe, enjoy a winter wonderland with great food and cocktails. Walk outside your igloo and roast s’mores over the outdoor fire pits, and stay warm and cozy wearing plush robes and blankets.

  1. Osteria Via Stato

Located on 620 N. State Street in downtown Chicago, Osteria Via Stato is a quaint Italian restaurant that was inspired by the Italian Alps for its outdoor dining experience. Your personal heated outdoor greenhouse can seat up to four people. And of course, Italian treats abound. The kids will absolutely love the classic cheese pizza topped off with a gelato dessert.

  1. Park & Field

Looking for something sporty? You’ve got it at Park & Field! This is a sports and club eatery located at 35909 W. Fullerton Avenue in Logan Square. Open throughout the year, it features fire pits, patio heaters, a heated yurt, and tents where you can enjoy the warmth. The kids’ menu features the classic mac and cheese bowl. While you can bring your own blankets (BYOB), you can also purchase them on-site. The four seasons rugby room will be enclosed during the winter and heated, making it the perfect opportunity to gather with friends and family.

  1. Pilsen Yards

Pilsen Yards’ entire east patio wall is open to the outdoors. Even though it doesn’t feature a kids’ menu, the tacos, nachos, or sweet corn tamales more than make up for this. This fun and festive dining experience is located at 1163 W. 18th Street.

North/northwest suburbs

  1. Buffalo Creek Brewing

For those looking for an authentic German Alpine Biergarten experience, Buffalo Creek Brewing could be the right place for you! Located on 360 Historical Lane in Long Grove, this brewery transforms into a winter oasis. Kids will love the outdoor games and homemade non-alcoholic sodas. But there’s something unique for the adults, too. Ranging from fire pits, table heat lamps, mood lighting, blankets, throws, and scarves for sale, the holiday decor is all set against the backdrop of a glorious pine forest.

  1. The Glen Club

The Glen Club offers dining or lounge igloos and the view from these is absolutely stunning. Overlooking the golf club in Glenview, this dining experience can be found at 2901 W. Lake Avenue. The dessert options are simply divine and feature the rich and decadent chocolate fondue and s’mores kit.

South suburbs

  1. The Forge

Couples or groups of four can spend up to 90 minutes enjoying a candle-lit meal in a stunning igloo while taking in the sights and sounds of the picturesque Forge Quarry with the Eight Towers Adventure ahead in the distance. This lovely location can be found at 1001 Main Street, Lemont.

  1. DIGS on Canal

Looking for a more spacious place to lounge? Try DIGS on Canal in Lemont. Near Lemont’s I&M and Ship and Sanitary Canals, you can enjoy sumptuous weekday or weekend meals. Its menu is filled with kid-friendly meals including burgers, pizza, and mac and cheese. The latter is available in a build-your-own format or as a flight. Adults, on the other hand, can order some tasty Pollyanna beer.

  1. Freedom Brothers Pizza

A pizza joint in Plainfield? Why not? Great for a whole-family experience, you can have lunch or dinner there with pizzas, sandwiches, and salads available to suit any taste bud. There are also many customizable choices for children. And of course, the dessert is absolutely divine and features dessert pizza, cotton candy, and s’mores dips.

Western Suburbs

  1. Bien Trucha

Situated on 410 W. State Street in the Geneva suburb, Bien Trucha is a suburban Mexican restaurant. Offering personal outdoor dining pods with lights, music, and heaters, it’s perfect for the entire family! Signature treats include traditional guacamole, pelote dip, various taco options, and churro bites.

  1. Gia Mia

The Geneva and St. Charles suburbs bring us Gia Mia! This restaurant features igloos and great Italian food. But that’s not all! The kids’ menu is absolutely divine and includes treats such as calzones and meatballs, mac and cheese, cheese pizza, and so much more.

  1. Stray Hen Cafe

Looking for somewhere to dine out in Elmhurst? Try the Stray Hen Cafe! It has an extensive menu and serves breakfast, brunch, and lunch. Kids can enjoy the waffle flights, Mickey Mouse pancakes, and more than two dozen different egg dishes - ranging from skillets to omelets to sandwiches. Adults, on the other hand, can choose from a dozen brunch cocktails in igloos on the sidewalk patio.

  1. Fiamme Pizza

Near downtown, Naperville features winter villas and greenhouses to keep guests warm. This is a classic Neapolitan pizzeria, offering villas that seat six. Meanwhile, greenhouses hold up to four guests. You and your loved ones can enjoy pasta entrees and wood-fired or Detroit-style pizzas. All this can be topped off with decadent desserts such as the Mount Vesuvio brownie sundae.

Final thoughts

Wrapping up our list of the 14 best igloo places in and around Chicago for you to enjoy on a cold, wintry day, it’s worth mentioning that you don’t have to worry about transportation. We all know that parking and even finding the venue can be a difficult and cumbersome task. But why spoil your day or evening?

At Bus Connection, we offer a variety of buses to get you to and from your chosen location safely and in good spirits so that you can enjoy your time out with your loved ones. Don’t hesitate to reach out to us and we’ll ensure you’re dropped off where and when you need it smoothly and seamlessly. We’re just a call or a click away so feel free to get in touch!