10 Best Chicago Wine Delivery in 2024: Only the Finest

If you’re looking for Chicago wine delivery, you have a wide variety of choices. It's crucial to select a service that aligns with your preferences for convenience, variety, and price. Making the right choice ensures a satisfying wine experience tailored to your lifestyle.

I researched many wine delivery services. My review focused on key aspects such as selection diversity, delivery efficiency, pricing, and customer service. Based on these criteria, I've curated a list of the top 10 services offering Chicago wine delivery.

Firstleaf is my top pick for Chicago's wine enthusiasts. It stands out with its extensive selection of award-winning wines, stellar customer service, and competitive pricing. But every service on this list has something to offer, so you’re sure to find an option that meets your individual needs. Read on to find the Windy City’s best wine delivery. 

The Best Chicago Wine Delivery Services Reviewed

1. Firstleaf – Best Chicago Wine Delivery Service 2024

Firstleaf's selection includes many award-winning wines recognized by prestigious wine competitions and publications. The Sonoma County Cabernet Sauvignon and the South African Chenin Blanc pictured above won multiple gold medals. But despite all those awards, Firstleaf offers its wines at very reasonable prices. 

You start your subscription with a 13-question tasting quiz that helps Firstleaf understand your palate preferences. You also have the opportunity to give each bottle you receive a thumbs-up or thumbs-down rating. Firstleaf uses this information to deliver shipments tailored to your tastes. With just 3 ratings, Firstleaf claims it can predict your wine taste with 98% accuracy.

The complimentary Wine Concierge service offers personalized wine consultations. You get expert assistance in finding new wines that match your palate. Our expert reviewer was very impressed by Firstleaf’s customer service.

You can also take advantage of Firstleaf’s Wine School. Located on Firstleaf’s website, the Wine School covers topics like winemaking, pairings, and varietals. You’ll find lots of informative articles about the wine you’re drinking and about wine in general. It’s a great way for novices and more seasoned wine lovers to expand their wine knowledge.

Selections include a variety of international wines as well as American favorites. While you’ll find a lot of popular varietals like Cabernet Sauvignon and Pinot Noir, you’ll also find some unfamiliar varietals as well as wines from lesser-known wine producing regions like Chile and South Africa.

In addition to its wine selection, Firstleaf offers thoughtful gift options like wine bundles and gift cards. You can choose from a variety of European and American wineries with a great selection of grape varietals. And if you’re still not sure what to send, Firstleaf also offers E-Gift cards from $25 to $200.

Firstleaf is also committed to sustainability. Its shipping process is carbon-neutral, and all packaging is 100% recyclable. There’s even a selection of vegan and eco-friendly wines on its menu, so eco-conscious and plant-based Chicagoans can find bottles suited to their needs. 

Firstleaf prices start at $7.49 per bottle, and most bottles are priced under $30. With your Firstleaf subscription you get a 30% discount on any orders, as well as a 100% satisfaction guarantee on every bottle you receive. There is a 6-bottle minimum on all Firstleaf orders.

2. Naked Wines – Best Wines from Independent Wineries

Naked Wines deals directly with independent wineries. This not only cuts out the middleman and lets Naked Wines sell bottles at discount prices. It also gives you access to wines from smaller vineyards that you won’t find at Chicago wine retailers. 

Your Naked Wines Angel membership supports independent and family-owned vineyards. Every month you put $40 into your Angel account. Naked Wines uses this money to support independent vineyards. When you are ready to order wine, that money is credited toward your purchase and you receive the wines at a substantial discount. 

Every month Naked Wines experts taste thousands of wines from hundreds of vineyards. Only the top 5% are chosen. This rigorous selection process ensures that you find only the best wines in your Naked Wines box. You can learn more in our detailed Naked Wines review.

Naked Wines provides customer ratings for each wine, which is a huge help in the selection process. You get to choose your own bottles, which gives you a lot of freedom but can be daunting given the enormous number of available wines. Seeing what other wine lovers thought about each bottle can help you narrow down your choices.

If you’re not familiar with different varietals and wine types, Naked Wines offers a simple solution with its filtering options. You can choose wines by style. For example, you can look for a fruity red, a big red, or a smooth red. This makes the selection process easier even for novices. 

Angel members also get access to the Naked Wines message board. This online community puts you in touch with other Angel members, Naked Wines staff, and winemakers who are supported by your Angel dollars. You can learn more about wine from wine experts and even from the people who made your favorite bottles. 

Prices begin at $7.99 per bottle, with a good selection of wines under $10 and a few premium options at over $100. There is a 6-bottle medium. Angel members receive discounts of 40% to over 60% on their purchases. 

3. Vinesse – Best for Wines at All Price Points

Vinesse has over 20 years of experience in selecting small-batch wines. You’ll find bottles from family-owned wineries in California and from around the world. Our reviewer was highly impressed by the quality and variety of wines on offer at Vinesse. 

Every order from Vinesse comes with detailed tasting notes that guide you through the wines flavors, notes and aromas. Vinesse’s suggested food pairings can be especially helpful for Chicago wine lovers who want to enjoy their wines with meals from Chicago’s diverse culinary scene. 

Vinesse showcases an impressive selection from celebrated US wine regions. About 70% of its offerings are domestic, while the remaining 30% are sourced internationally. You’ll find wines ranging from less than $15 a bottle to premium wines costing over $75, with bottles ranging from light, sweet dessert wines to fruity and forceful reds.

You can choose between a la carte wine orders and ongoing memberships. If you’re intrigued by Vinesse but still aren’t quite sure you want to commit to a subscription, a 1-time order lets you try out Vinesse’s offerings for yourself before making that decision. Vinesse even offers Sampler bundles that let you try out different wine styles and flavors. 

You can choose between a 3, 4, 6, or 12 bottle subscription, with delivery every 1, 2, or 3 months. While you can choose reds, whites, or a mixture of both, you can’t select individual bottles. But you can always add extra bottles or wine bundles from the store. 

If you have wine-loving friends, Vinesse also offers gift cards, subscriptions, and wine bundles. The broad menu means Vinesse has great presents for novices and seasoned wine enthusiasts alike. All Vinesse orders are shipped in recyclable packaging, and many of the wineries Vinesse works with use sustainable farming methods. 

Vinesse prices start at $10.00 per bottle, and there is no minimum order. Shipping is free on orders of 12 bottles or more. Smaller orders incur a $16 shipping fee and $5 handling charge per delivery.

4. Bright Cellars – Best Personalized Wine Matching

Bright Cellars determines your wine preferences with an advanced quiz crafted by its founders. If you’re worried about taking an advanced quiz, relax! The questions are simple and you can answer them in a few minutes. The website, like the quiz, is also well organized and user-friendly. Navigating through its selection of wine bundles is easy. 

Wines are chosen by a certified sommelier and a team of Bright Cellars wine experts. They note the body, sweetness, bitterness, astringency, and other characteristics of each wine. That data is then used to determine what wines are best suited to each customer’s palate.

If you don’t feel excited about any bottle Bright Cellars recommends for your subscription box, you can swap with a different option that is also provided based on your answers. You get the best of both worlds with computerized recommendations, expert suggestions, and customer flexibility.

In addition to its subscriptions, Bright Cellars offers wine bundles a la carte. Our Bright Cellars reviewer noted that the bundles were designed for everything from summer parties to formal dinners. But you should note that the bundles are curated so you can’t mix and match bottles

You can also choose from a selection of ready-to-drink margarita bundles. All you need is some ice and rock salt for the rim and you’re set for a party. If you're in the mood for something other than wine, Bright Cellars has you covered. 

The Bright Cellars website also includes a dedicated section for wine education. There are many articles to help you understand wine flavors, pairings, and so on. Along with an algorithm that takes the guesswork out of choosing wines, this makes Bright Cellars a great choice for wine beginners.

Prices start at $10.00 per bottle, and there is a 4-bottle minimum order. You can choose between a 4, 6, or 12-bottle subscription. Shipping is free on orders of 6 bottles or over, and subscribers get a 20% discount on all wine bundles at the store. 

5. Wine Insiders– Best Choice of Inexpensive Wines 

Wine Insiders is a great choice for budget-conscious Chicago wine lovers. If you’re looking for excellent wines that won’t break your bank, you’ll find selections from winemaking regions around the world, with an extensive range of wines under $20. 

Whether you're in the mood for a crisp Chardonnay, a robust Cabernet Sauvignon, or something in between, Wine Insiders has you covered. Our reviewer felt that Wine Insiders offered a great selection of wines at extremely affordable prices. 

Wine Insiders provides comprehensive details about each bottle's background and tasting notes. You not only learn about flavor profiles and pairing recommendations, you get information on the varietals, regions, and producers. You’ll find wines from classic regions like Italy and Portugal alongside less well-known regions like Morocco and Mexico.

You’ll even find specialty wines like vegan and organic wines, as well as a selection of canned wines and ready-to-drink cocktails. Chicago wine drinkers on specialized diets will find wines that meet their needs without spending a fortune.

The Wine Insiders curatorial team has over 50 years of combined wine experience. They put that expertise to work finding budget wines that punch well above their price point. Only 3% of the thousands of wines that Wine Insiders curators try each year are selected for sale, so you know you’re getting the cream of the crop. 

You’ll even find a selection of wines curated by Martha Stewart. If you miss the now-closed Martha Stewart Wine Club, you’ll love her Wine Insiders selections. The Elegant European Rosé Trio pictured above features fine French rosés that meet Martha’s demanding standards of approval, and are more nuanced and complex than most rosés at their price.

You get bimonthly deliveries of 3, 4, 6, or 12 bottles. Everything that arrives on your doorstep – the shipping box, cardboard separators, and bottles – is recyclable. You can choose between red, white, or mixed orders. You can also order a la carte, with a 3-bottle minimum order. Prices start at $8.99 per bottle.

6. The California Wine Club – Best Artisan Wines from California & Beyond

The California Wine Club is a great choice for fans of California wine. With a legacy spanning 30 years, this family-run business has mastered the art of curating the finest California wines from small, family-run vineyards and delivering them to your doorstep.

With its 6 different wine clubs, The California Wine Club offers options that cater to nearly every wine lover's palate. Whether you prefer reds, whites, or a mix of both, you'll find a club that suits your taste and your pocketbook. And while it specializes in wines from the Golden State, you’ll also find high-quality international wines and wines from the Pacific Northwest. 

The Case Club offers 12-bottle shipments for $168, or $14 per bottle. This is a great price for boutique wines. For connoisseurs, the Aged Cabernet Series sends a pair of $140 bottles of 7-12 year old cabernets. Monthly, bimonthly, or quarterly subscriptions are available. And if you reorder a wine you like in the California Wine Club store, you get a discount.

In addition to personal subscriptions, The California Wine Club also has gift wine subscriptions, gift cards, and eGift certificates, as well as branded corporate gifts for those seeking unique ways to connect with business partners. You can learn more about The California Wine Club’s offerings in our detailed review.

You also get a subscription to Uncorked magazine, which offers you armchair tours of different California wineries along with food pairings, and recipes. And if you’re thinking about visiting California, you can schedule a stop at 1 of The California Wine Club’s VIP tours and tastings. It regularly offers these events at the California wineries that provide it with bottles. 

If you’re on the fence about commiting to a subscription, The California Wine Club's "Love It" guarantee ensures that your journey through California's vineyards is risk-free. If you don't love a bottle, the service will replace it.

Prices start at $10.99 per bottle. A $16 shipping fee and $5 handling fee apply to every order with fewer than 12 bottles.

7. Wine Awesomeness – Great Mystery Wines

Wine Awesomeness has wines that will delight both beginners and wine enthusiasts. So, whether you're just starting your wine journey or are already well-versed in the world of vino, Wine Awesomeness aims to delight your palate. 

One of the standout features of Wine Awesomeness is its impressive wine list. Whether you prefer a crisp Sauvignon Blanc or a bold Cabernet Sauvignon, Wine Awesomeness has something for every palate. Our Wine Awesomeness reviewer spoke highly of the selection.

The Discovery Wine Club brings you a monthly supply of wines to your doorstep. You can decide whether to choose your own wines or accept the selections from the Wine Awesomeness experts. While Wine Awesomeness doesn’t have a quiz, it uses your reviews and ratings to curate bottles for you. You can also read the reviews from other subscribers.

If you like surprises but don’t feel like subscribing, you can always buy a Wine Awesomeness Mystery Box. With a Mystery Box you get a blind selection of wines at a significant discount. It’s an exciting way to explore new wines you might not have tried otherwise. If you don’t want that big a surprise, Wine Awesomeness also offers Mystery Bottles. 

The Back Label, the Wine Awesomeness companion blog, is a great resource for those who want to enhance their wine knowledge. You’ll find recipes, pairings, and interviews with chefs, sommeliers, winemakers, and other wine personalities. Even if you’re not a subscriber, you can take advantage of the information Wine Awesomeness freely makes available.

You’ll also find plenty of gift options for wine-loving friends. You can give gift subscriptions and e-gift cards. Or you can choose from the many wine bundle options that Wine Awesomeness offers, like the White Wines to Pair with Cheese 12-pack pictured above. 

Prices start at $13.25 per bottle, and there’s a 3-bottle minimum. Subscribers get 20% off on all a la carte orders. 

8. Macy’s Wine Shop – Great for Curated Sets and Gifts

Macy’s Wine Shop stands out as a top choice for Chicago wine lovers. It offers an affordable and carefully curated selection of satisfying wines. Whether you’re looking for a single bottle or a wine bundle, Macy’s Wine Shop has what you need. 

Macy's Wine Shop takes its wine selection seriously. Every bottle offered is meticulously chosen by an expert tasting panel, which includes a sommelier and a chef. This commitment to quality ensures that you're getting the best Chicago has to offer in terms of wine. Every order includes detailed tasting notes for each bottle.

While you can subscribe to Macy’s Wine Club for deliveries, you can also shop for 1-time orders. This makes it a great choice for both wine lovers looking for occasional purchasers and those who want regular wine deliveries. Our reviewer spoke highly of the many options available.

For those seeking unique experiences, Macy's Wine Shop offers themed wine bundles like Thrill of the Grill and Global Tasting Case. These curated collections are designed to enhance your wine journey by bringing you bottles that complement specific occasions or cuisines. It's a thoughtful touch that elevates your wine-drinking experience.

A Macy's Wine Shop's Club subscription is great for those who want to expand their wine collection. You'll receive a box of 12 expertly selected reds, whites, or a mix every 12 weeks. And you also get bonus summer and winter boxes for grill-outs and holiday parties. To sweeten the pot, you get an introductory trial box of 6 bottles for just $49.99!

Speaking of holidays, you can also find curated wine sets and gift options. If you want to make a lasting impression on your wine-loving friend, Macy’s Wine Shop can help make your special occasions even more special. Prices start at $10.99, and there's a 2-bottle minimum order. 

9. Monthly Clubs Wine Club – Great for Wine & More

Monthly Clubs Wine, established in 1974, is the first and oldest wine delivery service. Current owner Paul Kalemkiarnian Jr. learned the business from his father, the Monthly Clubs founder. You’ll find subscription options and wines at every price point. 

Wines are curated by a team of skilled sommeliers. These experts choose the best-tasting wines for your enjoyment. Our expert reviewer was very impressed with the quality of wines available at Monthly Clubs Wine.

You can select from 4 distinct monthly wine clubs: The Premier Series, The Bold Reds, The Masters Series, and The Collectors Series. Whether you crave bold reds or prefer exploring wines from prestigious wine regions, Monthly Clubs Wine has got you covered.

The Premier Series Wine Club is the most popular subscription. Each month you get 2 estate-bottled, limited-production wines from boutique wineries. It’s a great way for Chicago wine lovers to expand their palate and explore unique, high-quality wines from around the globe.

If you're looking for premium rare and aged wines, you’ll love the Collectors Series Wine Club. It offers a selection of premium, aged wines that you can drink now or cellar for added depth and complexity. And red wine lovers will get a steady supply of fine wine with a subscription to the Bold Reds Wine Club.

Monthly Clubs Wine Club also has great curated gift sets. You can choose 2-6 bottles of sweet, organic, Bordeaux, and other wines. And if you need a gift for a friend who doesn’t care for wine, you can always find something at the other Monthly Clubs. 

Beyond wine, Monthly Clubs Wine offers a variety of other monthly clubs, catering to different tastes. Whether you're into cheese, chocolate, flowers, beer, or cigars, you can find a club that suits your interests. 

Prices start at $20.98 per bottle, with a 2-bottle minimum order. Monthly Clubs Wine offers a 100% satisfaction guarantee, promising “You’ll never pay for a wine you don’t love.”

10. Winc – Great Eco-Friendly Everyday Wines

Winc is a good choice for Chicagoans who are looking for eco-friendly wines. It collaborates with vineyards that prioritize sustainable wine production practices. Winc is also a member of the 1% for the Planet organization, which donates 1% of sales to environmental causes. And our reviewer noted that all Winc shipments use recyclable packaging. 

With a selection of around 50 wines, Winc provides a decent variety to choose from. Approximately a third of its menu consists of domestic wines, primarily sourced from California. The Restless Earth 2020 bottle pictured above is an organic French wine that goes great with burgers and red meat dishes. 

You can either handpick your preferred bottles or take advantage of Winc’s on-site quiz. The quiz helps Winc recommend wines that align with your taste preferences, making the selection process easier for you.

Winc offers filters to help you shortlist your wine choices based on varietal, palate, and other factors. The Values filter includes selections like Certified Vegan, Organic Wines, and Organic Grapes. But you should note that you can't filter by country, which might be a problem if you’re seeking wines from specific regions.

One aspect to keep in mind is that Winc's popular wines tend to sell out quickly. If you discover a wine you love in your Winc box, it's advisable to order it promptly to avoid disappointment. It's also worth noting that Winc doesn't offer a la carte orders, meaning you need to become a member to access their wine selection. 

Winc operates on a subscription model, with a monthly cost of $59.95. In return, you receive 60 Winc credits, which you can use to purchase your favorite bottles. Prices start at $12.00 per bottle, with a minimum order requirement of 3 bottles. Shipping is free on orders of 4 bottles or more and you get a 10% discount on orders of 12+ bottles.

Quick Comparison Table

Tips for Choosing the Best Chicago Wine Delivery 

With all these wine delivery services to choose from, finding the 1 that’s right for you can seem overwhelming. Here are some of the pointers I used when listing the best Chicago wine delivery services. 

• Find your price point: Wine delivery services offer wines at various price ranges. Firstleaf stands out with many award-winning wines priced between $15 to $30 per bottle. This ensures you can enjoy quality wine without breaking the bank.

• Check shipping costs: Wine bottles are both heavy and fragile, which makes shipping expensive. Naked Wines provides free shipping on orders over 6 bottles. This can save you a considerable amount in the long run.

• How much wine do you drink each month?: If your subscription is too big, you can soon run into wine storage issues. Vinesse offers a 3-bottle subscription and makes it easy for you to pause shipments if you already have enough wine in the house. 

• Consider your preferences: When choosing a wine delivery service, check the wine list to ensure it aligns with your preferences. Bright Cellars, which uses an algorithm to select wines tailored to your taste profile, is an excellent choice for wine novices. 

FAQ

What’s the best Chicago wine delivery?

Firstleaf is my choice for the best Chicago wine delivery. It has an excellent selection of wines at very reasonable prices. That, combined with the superior customer support offered by its Wine Concierge service, puts Firstleaf at the top of our list.  

Can wine delivery save you money? 

A wine delivery subscription can definitely save you money. Wine clubs cut out middlemen like bulk distributors, sales managers, and retail store employees. When you sign up for Naked wines, you’ll find excellent wines available at a 40-60% discount.  

What’s the best wine delivery for beginners?

I recommend Bright Cellars as the best wine delivery service for wine newcomers. The Bright Cellars algorithm takes the guesswork out of buying new wines and helps ensure you’ll get new wines that are perfectly suited to your tastes.  

Best Chicago Wine Delivery in 2024 — Final Score