Wine Tasting in Des Plaines, IL

$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

$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

$38 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 $38

$16 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 $16

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

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

Second City Tours - Chicago Water Tower


$100 $50

$37 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 $37

Wine Tasting for 4, 10, or 20 with 63% 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 $15

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

$62 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 $62

Wine & Cheese Tour of Chicago with 12 Tastings and Pairings for 1, 2, or 4 from Best Tours (Up to 62% 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 $44

$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

$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

$11 for $20 Worth of Pub Food at The Howard Street Inn

Howard Street Inn


Menu includes deli and grilled sandwiches, Angus burgers, pizza, craft and domestic brews, and specialty drinks

$20 $11

$17 for $30 Worth of Tropical Appetizers and Tiki-Bar Drinks at Hala Kahiki

Hala Kahiki

River Grove

Tropical cocktails named for Pelé and coral reefs poured in Polynesian-themed bar opened in 1963

$30 $17

30% Cash Back at Tuckers on Grand

Tuckers on Grand

Northwest Side

Claim this deal and get 30% cash back rewards when you pay with your linked Visa card at Tuckers on Grand

$0 $0

Pub Fare at Union Ale House (48% Off). Two Options Available.

Union Ale House

Prospect Heights

Pair craft beer with menu items like saganaki, drunken nachos, salads, pizza, ribs, pork chops, and signature sandwiches

$20 $11

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

25% Cash Back at Game 7 Bar and Grill

Game 7 Bar and Grill


Claim this deal and get 25% cash back rewards when you pay with your linked Visa card at Game 7 Bar and Grill

$0 $0

Two Well Drinks and $10 in Tokens at Emporium Arcade Bar (Up to 60% Off). Two Options Available.

Emporium Arcade Bar

Multiple Locations

Visitors juggle drinks and joysticks at the arcade bar’s two locations, where vintage video games and pinball tables abound

$20 $8

Halloween Bar Crawl on October 28 or 29 or Trolley Bar Crawl: Crawl-o-ween on October 29, at 8 p.m.

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

Multiple Locations

Don creative Halloween costume, then walk or hop on a trolley to hit Chicago bars featuring drink specials, scavenger hunts, and prizes

$17.36 $8

American Food for Two, Four, or More at MT Barrels (48% Off)

MT Barrels


Start your meal with a cup filled with bacon and then get a burger with a patty dipped in buffalo sauce and topped with blue cheese

$20 $11

Select Local Merchants

  • Harry Caray's Italian Steakhouse
    Harry Caray's Italian Steakhouse offers a cozy atmosphere for you to enjoy a glass of wine or two. If you prefer to eat healthy, you'll find tons of fresh selections on Harry Caray's Italian Steakhouse's menu. Anyone can unwind in the bar bar, where televisions cater to the sports enthusiast and fine wines beckon the grape fanatic. Save money on a sitter — kids are welcome to join the table at this bar. Got a big family? Tons of friends? An entire soccer team? Consider the private room at Harry Caray's Italian Steakhouse, where large groups can get together to celebrate life's biggest milestones. Dine under the sun (or stars) at Harry Caray's Italian Steakhouse with their charming outdoor seating. Wifi here is on the house. Take advantage of the bar's reservation system, and book a table for your party. Casual clothing is the name of the game at Harry Caray's Italian Steakhouse, where suits and ties won't be spotted for miles. Want to enjoy this bar without the wait? Get it to go. You can also have Harry Caray's Italian Steakhouse cater your next event. Free parking is available right next door. If your preferred mode of transit is of the two wheel variety, you're in luck — there's tons of bike parking outside the bar. A night out here can be a bit pricey, so prepare to shell out a bit more. The bar is open from morning through evening, but the dinner menu serves the tastiest reviews. For the best wine in town, be sure to stop by Harry Caray's Italian Steakhouse. So when you're looking for the perfect blend of flavor and familiarity, the star-studded fare at Harry Caray's Italian Steakhouse is sure to hit the spot. Steak-lovers rejoice! Getting the juiciest, most flavorful steaks in town is easy when you stop in for a meal at Harry Caray's Italian Steakhouse.
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    Rosemont, IL US
  • Flight Wine Bar
    Oenophiles rejoice! Flight Restaurant and Wine Bar offers an amazing wine list and great ambience for sipping the night away. Flush with wines from around the world, drink from the restaurant's extensive list of reds and whites. The bar also has TVs, so patrons can enjoy their glass while following up on the latest scores. Big groups always enjoy coming to Flight Restaurant and Wine Bar. Flight Restaurant and Wine Bar offers a free wifi hot spot — perfect for surfing the web or getting a little work done. Don't stay cooped up on a beautiful summer day! At Flight Restaurant and Wine Bar, you can dine outdoors on their lovely patio. People tend to swarm the restaurant on Fridays and Saturdays, so be sure to reserve space for your party ahead of time. At Flight Restaurant and Wine Bar, "dress to impress" is a thing of the past, and jeans are the new norm. That's right! Flight Restaurant and Wine Bar will bring their delicious food to your house for any occasion. The food is prepared and packaged, just waiting for your pickup. Don't forget to tip the valet — Flight Restaurant and Wine Bar's Tower Dr location provides a parking service. Cyclists are in luck. Flight Restaurant and Wine Bar provides bike parking. Prices at Flight Restaurant and Wine Bar are moderate — most diners plunk down about $30 per meal. When it comes to wine, Flight Restaurant and Wine Bar has some of the best selections in town. Come on over today and check out the latest offerings. The friendly staff at Flight Restaurant and Wine Bar are ready and waiting to cook and serve your favorite American meal. If you're seeking a highly-rated American restaurant in the area, look no further than Flight Restaurant and Wine Bar.
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    Glenview, IL US
  • Jolanes
    With its epic wine list and charming interior, Jolane's is a great spot for a date or a night out with friends. Gluten-free and low-fat are not one in the same, but this place serves them both. With its long wine list and TVs in the bar area, the bar has enough to keep oenophiles and sports fans happy. Gather the whole family for a trip to this bar — everyone will find something to like (even the pickiest little eater) on the menu here. A great space for entertaining large parties, consider reserving the private room at Jolane's for your next big event. Get online gratis thanks to Jolane's' complimentary wifi. On warmer days, you can take advantage of Jolane's' al fresco patio seating. Fridays and Saturdays really bring in the crowds, so make sure there's space for you by calling ahead for a reservation. Whether you're coming from work or a ballgame, the dress code at laid-back Jolane's is come-as-you-are. Jolane's is known for serving great food, and they are able to serve it at your next event with their excellent catering. Carry-out is also available for those who prefer to enjoy this bar's cooking from the comfort of their own home. Save some cash on parking when you park in the lot adjacent to the restaurant. Jolane's s fare is so good, you ll want to sample everything on the menu (and with its middle-of-the-road prices, you can!). Jolane's accepts all major credit cards, including Visa, MasterCard, Discover, and American Express. Chow down on breakfast, lunch, or dinner fare at Jolane's — they're open for all three meals. Make your way over to Jolane's and enjoy a delicious and refreshing glass of red or white wine.
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    Glenview, IL US
  • Cooper's Hawk
    You'll find a wonderful selection of drinks from this restaurant's full bar to top off your meal. Little ones are just as welcome as their parents at this restaurant. Cooper's Hawk Winery and Restaurant is a local restaurant that accommodates both large and small groups. Free wifi is available as well. Reservations are recommended for those on a strict schedule. Cooper's Hawk Winery and Restaurant wants guests to dine in comfort, so save that stuffy suit for another date. Feeling a little shy? Carryout is available. At Cooper's Hawk Winery and Restaurant, drivers will appreciate the ample parking options in the area. Checks are bigger than average at the restaurant, so prepare your wallet. So whether you're on the hunt for something fancy or just an easy-drinking bottle, the wines at Cooper's Hawk Winery and Restaurant have plenty to offer. The best American dishes are cooked up by the great crew at Cooper's Hawk Winery and Restaurant, and they're waiting to serve you! So take your next meal to the next level and indulge in some great American eats at the highly-rated Cooper's Hawk Winery and Restaurant.
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    Arlington Heights, IL US
  • Wine With Me
    Oenophiles rejoice! Wine With Me offers an amazing wine list and great ambience for sipping the night away. Whether you prefer a deep red or dry white, the bar is home to a wide variety of wines from numerous regions around the world. Don't fuss with street parking. We've got some parking available. A mid-priced establishment, Wine With Me offers meals that typically cost about $30 or less.
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    Itasca, IL US
  • Lynfred Winery - Wheeling
    With its massive selection of varietals and styles, Lynfred Winery seems determined to make something for almost any wine drinker. The cellar brims with everything from bold, spicy reds to crisp and refreshing whites, as well as fruit wines made from apples, cherries, rhubarb, and pears. The grapes arrive from vineyards throughout California and Washington state, although the rest of the fruit typically comes from a bit closer to home, including growers throughout Michigan and Wisconsin. Despite this variety, the staff's commitment to approachable, fruit-forward flavors characterizes virtually everything that the winery makes. This dedication to easy drinking seems only natural given the winery's origins in a home basement. In 1975, Fred Koehler, along with his wife Lynn, decided to try to re-create the family wines his father and grandfather had made throughout the 1920s. The batches grew larger with each passing vintage, and, in 1979, Fred and Lynn chose to upgrade their homespun hobby into a commercial venture. Within six years, Lynfred Winery's creations began to appear in the national spotlight as they garnered awards and medals from wine competitions across the country. This attention allowed Fred to swell production even more, eventually expanding to a larger location in 1990. Fred and Lynn's legacy continues to inspire the staff as they operate a facility that creates more than 100,000 gallons of wine each year using as many as 80 varietals. These wines appear on restaurant menus, on retail shelves, and inside fish tanks throughout the Chicagoland area.
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    Wheeling, IL US