The Best Vineyard & Winery Wedding Venues in Pleasant Prairie, WI

The Best Vineyard & Winery Wedding Venues in Pleasant Prairie, WI

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3 Wedding Venues in Pleasant Prairie, WI

Vineyards, wineries
150-200 guests
Available on May 30, 2026
Quick responder
Chicago Winery 

5.0

Chicago, IL
  • Up to 225 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $20,000

Chicago Winery offers a vibrant setting in the heart of the city, perfect for couples seeking a unique and memorable wedding. The venue combines urban chic with winery charm, providing a warm and inviting atmosphere. Guests enjoy the in-house wine selection and customizable menus, ensuring a personalized culinary experience. The attentive staff and flexible event spaces cater to various wedding styles, making it easy to create a bespoke celebration. Chicago Winery is ideal for those looking to blend city sophistication with the intimate feel of a winery.

Why you'll love this venue

  • Allows pets
  • Flexible event spaces
  • Provides event staff

Venue considerations

  • Venue feels large for events with small guest lists
  • No on-premises lodging options
  • On-site parking not available
Awarded Best of Zola
Chicago Winery is a stunning wedding venue that provides a full service experience. An event coordinator is included in the package, who helps you plan your big day from beginning to end--Hulda was ours and we absolutely loved her! Since Chicago Winery is a restaurant, the food was outstanding and the staff well-versed. Their bar package is excellent, and they will work with you to bring in anything else you may need. This space is absolutely stunning from an interior design perspective, which allows for less decor and florals needed to achieve a dreamy look. If you're looking to have a downtown Chicago wedding, look no further than Chicago Winery!
Maryclaire C., a year ago
Quick responder
City Winery Chicago 

5.0

Chicago, IL
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $10,000

Celebrate your love with a romantic urban winery wedding! City Winery offers the ambiance and unique style of a rustic urban winery wedding with the ease of a full-service wedding venue. Our experienced events team is at your service to help you bring your dream winery wedding to life.

Why you'll love this venue

  • Pets can join the celebration
  • Space for a large guest list
  • Sophisticated wine experience

Venue considerations

  • Does not have a dance floor
  • Not wheelchair accessible
  • No free parking
City Winery Chicago was a fantastic venue for a friend and client's wedding! The team there was incredibly responsive, providing quick, detailed, and enthusiastic communication throughout the planning process. The space itself has a wonderful rustic industrial vibe that perfectly blends European winery charm. The team went above and beyond to ensure a great experience not just for our guests, but for the vendors as well. The vendor meals were delicious, and the overall atmosphere was warm and inviting. We couldn't have asked for a better wedding venue.
Lindsay J., 7 months ago
Quick responder
Pinstripes Oak Brook 

5.0

Oak Brook, IL
  • Up to 1000 guests
  • All-inclusive
  • Indoor & outdoor

Whether you are hosting a wedding reception, ceremony, bridal shower or bachelor(ette) party our dynamic ballrooms and private event spaces provide an upscale yet relaxed space for your special day. We host truly unique events and deliver sophisticated fun through combining our from-scratch Italian-America menu with the classic games of bowling and bocce ball. Let our talented event team work with you on a customized event to suit your personal style and help you bring your dream wedding to life to create a perfect day that you and all your guests will be sure to remember!

Why you'll love this venue

  • Flexible event spaces
  • Romantic vineyard setting
  • Provides a dedicated team on-site

Venue considerations

  • Does not allow pets
  • Not wheelchair accessible
  • No free parking
Awarded Best of Zola
We wanted a more casual wedding and pinstripes was perfect for that. The weather was perfect so we were able to have our ceremony outside on the patio and that area was perfect for the pictures! We had bowling during cocktail hour which our guests loved. The food was incredible and they did a great job managing our cake, decor, and everything we dropped off. The whole staff was so easy to work with and all of the meetings went so smooth.
Sonya S., a year ago

Location flexible? Discover venues near Pleasant Prairie, WI

About wedding venues in Pleasant Prairie, WI

Wisconsin offers incredible wedding venue diversity with everything from rustic countryside barns to sophisticated urban spaces. You'll be amazed by the natural beauty that creates stunning backdrops for your special day no matter which season you choose for your wedding.

How Much Do Wisconsin Wedding Venues Cost?

Wedding venues across Wisconsin typically cost between $1,500 and $15,000+ which aligns perfectly with the national average of $6,500-$12,000. Your total budget will depend largely on how many guests you invite. For 50 guests you're looking at about $18,004 while 100 guests jumps to around $30,000. With 150 guests expect to spend approximately $41,280 and 200 guests increases to $51,366. Larger weddings with 250 guests run about $61,453 and 300 guests reaches $71,540. The venue itself represents only about 16% of your total budget averaging $6,625 for a 150-guest wedding which means you're getting excellent value for your investment.

What Types of Wedding Venues Will You Find in Wisconsin?

Wisconsin's venue landscape offers genuine diversity you won't find in many other states. You'll discover authentic rustic barn settings with genuine wooden beams and charming countryside views. Lakefront properties along Wisconsin's impressive 15,000 lakes provide breathtaking water backdrops. Milwaukee features historic buildings with distinctive industrial charm that photographers love. For nature lovers botanical settings like Boerner Botanical Gardens offer lush greenery and seasonal blooms. Luxury resorts provide comprehensive amenities that handle everything from accommodations to catering all under one roof.

Which Wisconsin Regions Have the Most Accessible Venues?

The Milwaukee Area features Villa Terrace which provides a Mediterranean-inspired setting with beautiful gardens and stunning Lake Michigan views. You'll appreciate that this venue is fully wheelchair accessible making it ideal for guests with mobility needs. In the Madison Region The Tinsmith has transformed a 1915 facility into a modern industrial venue that combines accessibility with sound-absorbing design elements your guests will appreciate during speeches. Western Wisconsin offers Maidenwood in Maiden Rock nestled in a beautiful nature reserve with breathtaking views and complete wheelchair accessibility that can accommodate up to 200 guests comfortably.

Where Can You Find Wisconsin Venues with Outstanding Food?

South Second in Milwaukee features Saz's Catering as their exclusive caterer and you'll be impressed by their customized stations and exceptional food quality. Guests consistently rave about the dining experience which often becomes a highlight of the wedding day. Destination Kohler is known for elegant settings paired with truly world-class cuisine that many guests describe as the best food they've ever had at a wedding. The Madison Club offers beautiful waterfront views while their culinary team focuses on locally sourced Wisconsin ingredients that showcase the region's best flavors in every dish.

How Can You Maximize Your Wisconsin Venue Budget?

Cost CategoryAverage CostPercentage of Total
Venue$6,62516%
Catering$5,30013%
Flowers$5,33313%
Photography$4,33711%
Bar Services$4,24010%
Videography$3,4988%

September ranks as Wisconsin's most popular wedding month but you'll find substantial discounts if you book between November and April. Friday weddings typically save you 10-15% compared to Saturday events which can free up thousands for other aspects of your celebration. Many venues offer package deals that combine services for added value especially during off-peak seasons.

Which Wisconsin Venues Offer Enhanced Remote Participation?

Wisconsin Union in Madison offers comprehensive virtual event services that can significantly enhance remote participation for guests who can't attend in person. Their dedicated planning team will help you create an inclusive experience for everyone. Celebrations on the River in La Crosse has experienced event planners who excel at setting up interactive remote experiences that keep virtual guests feeling connected to your special day. Destination Kohler offers incredibly versatile spaces that support creative engagement with remote guests through fully customizable experiences tailored to your specific vision and needs.

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