Wine Tasting in Crestwood, IL

Wine Tasting for Two, Four, or Six at Downers Grove Wine Shop (Up to 53% Off)

Downers Grove Wine Shop

Downers Grove

Samples of six wines accompany light appetizers during tasting sessions for two, four, or six

$20 $10

$42 for a Winery Tour for Two with a Bottle to Take Home at Acquaviva Winery ($64 Value)

Acquaviva Winery

Maple Park

Tour a picturesque winery with striking architecture before selecting a bottle to take home

$64 $42

$19 for a Wine Flight and Cheese for Two at The Vino Cellar ($36 Value)

The Vino Cellar

South Itasca

Three white or red wine samples accompanied by a cheese plate

$36 $19

Entry to River North Wine Fest on Saturday, December 3, from CHI Life Events,48% Off

CHI Life Events

Moe's Cantina - River North

More than 35 wines glitter in glasses at this 21+ festival, which also offers gourmet cheeses

$55.59 $29

$42 for Wine Tasting for Two with Lunch and Two Bottles of Wine at Kickapoo Creek Winery ($67 Value)

Kickapoo Creek Winery


Fruit-forward wines using locally sourced grapes; lunches such as wild pacific salmon burgers, pastry-wrapped bratwurst, and turkey reubens

$67 $42

$21 for $35 Worth of Wine and Food at Illinois River Winery

Illinois River Winery

Illinois River Winery

Sample more than 30 handcrafted wines in the tasting room, which serves food

$35 $21

"Wine & Cheese Walk" - Any Sat @ 3:00pm Through Dec 31, 2016 (Reserve in Advance)

Second City Tours - Chicago Water Tower


$100 $50

Wine Tasting for 4, 10, or 20 with 50% Off In-Store Purchases at WineStyles (Half Off)



Wine tasting and education event features instructor-led tasting of six wines; sessions focus on region or styles

$40 $20

$49 for a Six-Bottle In-Home Wine Tasting for Up to 12 from PRP Wine International ($200 Value)

PRP Wine International


Wine enthusiasts sample up to six global wines in-home as a staffer expounds on the winemaking process and shares food-pairing ideas

$200 $49

Wine Tasting for 4, 10, or 20 with 50% Off In-Store Purchases at WineStyles Shorewood (Half Off)

WineStyles Shorewood


Wine tasting and education event features instructor-led tasting of six wines; sessions focus on region or style

$40 $20

$55 for a Two-Hour Wine Tasting for 12 to 16 People from Wines for Humanity ($250 Value)

Wines for Humanity

Online Deal

Professional wine advisor teaches guests to discern distinctive notes in six exclusive vintages and pair them with appropriate dishes

$250 $55

$119 for One-Year Ownership of Two Vines at Carneros Della Notte ($198 Value)

Own a Napa Vineyard

Carneros Della Notte

Learn how to tend and harvest grapes, access special vineyard events, and make your own wine from grapes that grow on your vines

$198 $119

Wine, Cheese, and Chocolate Tasting, Painting, or Jewelry Making for One at Ela'$ Wine N Slots (30% Off)

Ela'$ Wine N Slots

Oak Forest

Inside this cozy, Oak Forest spot, patrons sample wines, cheeses, and chocolates, painting, or making jewelry

$20 $14

In-Home Wine Tasting for Up to 12 with Six or Eight Bottles from PRP Wine International (Up to 67% Off)

PRP Wine International

Overland Park

Sample wine from around the world at home with help from a wine connoisseur

$150 $49

$349 for a One-Year Wine Club Membership with Two Cases of Wine from Paired Wine Co. ($600 Value)

Paired Wine Co.


Membership includes 10% off purchases in store, invites to wine-tasting events, $5 voucher toward self-serving wine machines, and more

$600 $349

$34.99 for Six Mini and Six Full-Size Bottles of Wine, Including Shipping from Tasting Room ($99.94 Value)

Tasting Room

Online Deal

Taste six mini bottles of wine, fill out a profile about your preferences, and then get six full-size bottles of wine based on the profile

$99.94 $34.99

Wine & Cheese Tour of Chicago with 12 Tastings and Pairings for 1, 2, or 4 from Best Tours (Up to 58% Off)

Best Tours

Best Tours

Stroll along the Magnificent Mile and through the Gold Coast as you sample 12 bites of cheese paired with sips of wine

$100 $49

$19 for an Online Wine Pairing and Tasting Course from Mixology Training ($595 Value)

Mixology Training

Online Deal

Learn how to examine and evaluate wines with your senses and how to create an exemplary dining experience by pairing wine with food

$595 $19

$69 for a Four-Course Chef's Tasting Menu with Wine for Two at Red Door Chicago ($120 Value)

Red Door Chicago


This friendly neighborhood spot dishes out refined, yet playful food such as bulgogi sliders and poutine with spring peas and curry gravy

$120 $69

$49 for an In-Home Wine Tasting for Up to 12 with Six Bottles of Wine from PRP Wine International (Up to $250 Value)

PRP Wine International


Wine consultants travel to homes, pouring samples six different bottles for groups of up to 12

$250 $49

$30 for a Taste of Italy Package with Four Bottles of Award-Winning Italian Wines from Heartwood & Oak ($103 Value)

Heartwood & Oak

Online Deal

The wines include a Tuscan white, Sangiovese red, Pinot Grigio, and Chianti DOCG, a status bestowed on only a handful of quality wines

$103 $30

$39 for a Six-Bottle Sampler of Award-Winning California Wines from A Taste of California ($89.94 Value)

A Taste of California

Online Deal

Six bottles of wines from throughout California, including a mix of reds and whites—all of which have won awards at various competitions

$89.94 $39

Bar Food at The Sock Bar -N- Grill (Up to 50% Off). Three Options Available.

The Sock Bar -N- Grill

The Sock Sports Bar & Grill

Pizza puffs, burgers, loaded cheese fries, and other classic bar food along with a full bar and sports on the big screens

$20 $12

Bar and Grill Food at Bottoms Up Bar & Grill (Up to 40% Off). Two Options Available.

Bottoms Up Bar & Grill


Guests munch on burgers or fresh seafood as live bands jam in an outdoor beer garden and sporting events flash across 25 TVs

$20 $13

Halloween Bar Crawl on October 28 or 29

Halloween Trolley Bar Crawl or Halloween Bar Crawl: Crawl-o-ween

Multiple Locations

Don creative Halloween costume, then walk to Chicago bars featuring drink specials, scavenger hunts, and prizes

$17.36 $8

20% Cash Back at Wise Owl Drinkery & Cookhouse

Wise Owl Drinkery & Cookhouse

Near West Side

Get 20% cash back on your first purchase and 10% cash back on all additional purchases

$0 $0

A Nightmare on Hubbard Street-The 5th Annual River North Halloween Costume Bar Crawl on Saturday, October 29, at 12 pm

A Nightmare on Hubbard Street – The 5th Annual River North Halloween Costume Bar Crawl

Bar Louie

Annual Halloween-themed bar crawl weaves through River North, with drink specials, live DJs, and a costume contest along the way

$27.95 $15

20% Cash Back at Rockin Horse Saloon

Rockin Horse Saloon

Barrett Brothers

Claim this deal and get 20% cash back rewards when you pay with your linked Visa card at Rockin Horse Saloon

$0 $0

Burger Meals and Draft Beers for Two or Four Scoreboard Bar & Grill (Up to 48% Off)

Scoreboard Bar & Grill

Scoreboard Bar & Grill

Nachos piled with beans, melted cheese, and homemade chili precede half-pound burgers, seven kinds of sandwiches, and thin-crust pizzas

$54 $28

Brewery Package for 2 or 4 with Beer Flights, Tour, and 32-oz Crowlers at Blue Nose Brewery (Up to 49% Off)

Blue Nose Brewery


New brewery taking the city by storm gives craft-beer lovers a behind-the-scenes look at the brewing process that includes six-beer flights

$54 $29

Select Local Merchants

  • Cooper's Hawk Winery & Restaurant
    Enjoy a selection of white and red vintage wines at Cooper's Hawk Winery and Restaurant. Cooper's Hawk Winery and Restaurant's low-fat and G-free items make it easy to eat right. Enjoy a glass of fine wine and some television entertainment in the restaurant bar area. This restaurant is more than willing to accommodate families, so kids are welcome to tag along. Perfect for parties on the larger side, Cooper's Hawk Winery and Restaurant also has a private area available for use. Free wifi is available as well. Enjoy the beautiful weather while you chow down — with outdoor seating, Cooper's Hawk Winery and Restaurant is a great summer destination. Weeknights are often swamped, so plan ahead and make a reservation to avoid the restaurant's rush. At Cooper's Hawk Winery and Restaurant, business casual is the norm, so save your suit and tie for another day. Cooper's Hawk Winery and Restaurant can also cater your next party; call today for details. Just through the door at this restaurant, you can claim your food. No delivery required. Looking for a deal on parking? Free parking is easily accessible in the parking lot next door. Cooper's Hawk Winery and Restaurant offers a nice selection of mid-range cuisine, so you can expect a meal there to cost about $30 or less per person. Breakfast, lunch, and dinner are all served at the restaurant, but reviewers rate the dinner menu the highest. There's no better way to celebrate Wino Wednesdays than with a glass of wine or two from Cooper's Hawk Winery and Restaurant. When you're craving a true American classic, such as a burger and fries, make your way over to Cooper's Hawk Winery and Restaurant. So when you just need a place to go, Cooper's Hawk Winery and Restaurant is the perfect restaurant serving up American classics in Orland Park. If you're seeking a highly-rated American restaurant in the area, look no further than Cooper's Hawk Winery and Restaurant.
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    Orland Park, IL US
  • Corner Joynt
    Enjoy a wine and cheese pairing at Corner Joynt, a local wine bar. Corner Joynt isn't just a restaurant, it's also a wine bar. Parking by the bar is a breeze, so feel free to bring your own set of wheels. Whether you enjoy a smooth red or refreshing white bouquet, they have it all at Corner Joynt. So head to the best barbecue joint in the neighborhood!
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    Summit, IL US
  • Starbucks
    For the perfect jolt of caffeine, look no further than Starbucks. Starbucks' low-fat fare and fresh offerings appeal to anyone searching for great taste and a healthy diet. Sunny day plus appetite equals the perfect time to head to Starbucks. Starbucks will be able to accommodate your large party. Get connected at lightning fast speeds with Starbucks' complimentary wifi. Or, take your food to go. Don't leave the car at home when you come in. We'll give you one of the great spaces in our parking lot. And for free. Bike parking is also available outside the coffee shop. Starbucks provides morning, afternoon, and evening service, so you can easily find time to dine. When you need a morning pick-me-up, make your way over to Starbucks for a cup of coffee.
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    Burr Ridge, IL US
  • Bottles
    Bottles also offers a wide-ranging wine list. With TVs in the bar area, you can catch the game while you enjoy a glass of Merlot. Pick up some bottles of liquor and spirits and expand your cocktail and tasting knowledge. There is ample parking located within the area, making your parking spot hunting quick and stress-free.
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    Lemont, IL US
  • Cafe Borgia
    An Italian experience right at home, Cafe Borgia will have you ordering seconds. Take a peek at the drink menu here, and make sure to sample something off the list. With its kid-friendly vibe, this restaurant is a great spot for families to chow down. Bask in the sun (or moon!) light when you dine on Cafe Borgia's outdoor patio. Get online gratis thanks to Cafe Borgia's complimentary wifi. If you plan to hit the restaurant on a Friday or Saturday, it's best to fend off the crowds by calling ahead for a reservation. Leave the suit and tie at home — Cafe Borgia is business casual all the way. The food is prepared and packaged, just waiting for your pickup. Can't get enough of Cafe Borgia's tasty dishes? They also offer a catering service for parties and events. Heading to Cafe Borgia for a tasty meal? Drive on over and park in a matter of seconds. Checks are bigger than average at the restaurant, so prepare your wallet. When in Rome, you do as the Romans do. When at Cafe Borgia, you eat as deliciously as the Italians do.
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    Munster, IN US
  • Rittergut Wine Bar
    Rittergut Wine Bar Restaurant & Social Club crafts the perfect wine, seafood, and steak experience, with seating that overlooks the Chicago River. Wine by the glass and bottle from the vineyards of Spain, Austria, France, and Italy complements charcuterie and imported cheese plates stocked with wild boar salami or herb-laden garrotxa goat cheese, much like the contents of an enophile's personal bomb shelter. The tasting bar and private wine rooms set the stage for uninterrupted swilling, while dining rooms bathed in amber light host feasts of lamb burgers seasoned with Moroccan spices. Arched ceilings draw the eye downward to exposed brick walls and hardwood floors indoors, and a riverside patio with dark wicker booths and wooden tables perch patrons over ebbing crests and bottled messages that implore you to try the salmon.
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    Chicago, IL US