• 3-night stay in a woodsy cottage in Sawyer, Michigan (sleeps up to 6), 5 minutes from Warren Dunes
• $100 gift certificate to Staymaker at Journeyman Distillery
• $50 gift certificate to Luisa's Swedish Bakery & Market
• $70 gift certificate to The Acorn Theater
• $50 gift certificate to The Local Pour
• $100 gift certificate to Four Winds Casino New Buffalo (dining and amenities)
• Hungry for Harbor Country cookbook

Southwest Michigan's Harbor Country is the string of small lakeside towns just across the state line: Sawyer, Harbert, Three Oaks, New Buffalo and their neighbors. It is the easy weekend escape North Shore families have loved for generations, and this package hands you a whole trip.

Your home base is a woodsy cottage in Sawyer, just five minutes from the towering dunes and Lake Michigan beach at Warren Dunes State Park. Spend the day climbing the dunes and watching the sunset over the lake, then head into town.

Grab a dinner at Staymaker, the restaurant at Journeyman Distillery in Three Oaks, catch live music or a show at The Acorn Theater, stop by The Local Pour, and pick up pastries for the morning at Luisa's Swedish Bakery & Market. A $100 Four Winds certificate adds one more night out in New Buffalo, and the Hungry for Harbor Country cookbook lets you bring the flavors home.

Good to know: Cottage valid 10/1/25-12/15/26, excluding 7/1/26-8/16/26. Subject to availability; book early. Limit 6 guests. Guests must follow the Airbnb listing's house rules and sign a rental waiver. Four Winds certificate is not redeemable for gaming.

• Ravinia lawn passes for 6
• Dinner and drinks for 6 at Ravinia's Treetop Restaurant

You're sitting in this package right now. Ravinia, North America's oldest outdoor music festival, is the heart of summer on the North Shore, and this package gives you and five friends the full experience.

Start your evening with dinner and drinks for six at the Treetop Restaurant, with no picnic to pack and no cooler to haul. Then head out to the lawn to spread a blanket under the trees and enjoy a concert on one of the most beautiful summer evenings you'll have all year.

Good to know: Subject to Ravinia's scheduling and availability. Please coordinate your date with CASA Lake County.

• 2 tickets to Paul McCartney in Chicago on November 25
• One-night stay at The Hoxton, Chicago on November 25
• Dinner for two at Sepia with wine pairings, gratuity included

Some nights you remember forever. Here is a once-in-a-generation concert, a world-class dinner, and a stylish hotel room so no one has to drive home, all on the same night.

Begin with dinner for two at Sepia in the West Loop, one of Chicago's most celebrated restaurants, with wine pairings and gratuity already taken care of. Then see Paul McCartney live with two tickets to his November 25 Chicago show, and sing along to decades of Beatles and Wings classics with a full arena.

When the encore ends, retreat to The Hoxton in the heart of Fulton Market for the night. Sleep in, grab brunch in the neighborhood, and relive every song.

Good to know: Concert and hotel are both on November 25 only. Sepia date to be scheduled with the restaurant.

• Sunset sail for 6 with cocktails aboard the Grand Soleil
• Dinner and drinks for 6 at the Chicago Yacht Club
• 4-hour pontoon boat rental on the Chain O'Lakes from Off the Chain Rentals (Antioch)

Two unforgettable days on the water. Gather five friends for an evening sail on Lake Michigan aboard the Grand Soleil, with cocktails as the sun sets behind the Chicago skyline. Back on land, continue the evening with dinner and drinks for six at the historic Chicago Yacht Club.

Then trade the big lake for a lazy afternoon up north. Off the Chain Rentals provides a four-hour pontoon rental at Port of Blarney in Antioch, where you can cruise, swim and explore the Chain O'Lakes, the network of connected lakes along the Fox River.

Good to know: Sail and dinner must be arranged by August 2026. Pontoon rental subject to weather and availability.

• 2 tickets to a Writers Theatre performance
• $100 gift card to Guildhall Restaurant & Bar
• $25 gift certificate to Little Red Hen
• $50 gift card to Hometown Coffee & Juice

Everything you need for a perfect evening in downtown Glencoe, all within a short walk.

Begin with dinner at Guildhall, Glencoe's beloved restaurant and bar on Vernon Avenue. Then stroll over to Writers Theatre, the nationally recognized company whose striking theater building is one of the architectural gems of the North Shore.

The morning after, grab coffee and a fresh juice at Hometown Coffee & Juice (Glencoe, Winnetka or Lake Forest) and a treat from Little Red Hen.

Good to know: Writers Theatre: valid for As You Like It; book 48 hours in advance; expires 11/6/2025.

• 2 tickets to Northlight Theatre
• 2 tickets to Godspell by Music Theater Works
• $300 gift certificate to Francesco's Hole in the Wall (Northbrook)
• $25 gift certificate to The Claim Company (Northbrook)

Two date nights, one convenient stretch of Skokie Boulevard. Both shows play at the North Shore Center for the Performing Arts in Skokie.

Northlight Theatre is one of the region's leading professional theaters, and Music Theater Works' Godspell brings the beloved musical to life. Before each show, head up Skokie Boulevard to Northbrook: a $300 certificate to Francesco's Hole in the Wall covers a memorable Italian dinner, and The Claim Company is a longtime local favorite.

Good to know: Northlight: expires 4/30/2026; not valid opening nights or closing weekends. Godspell: show runs 10/23/25-11/16/25; return certificate by 10/23/25. Claim Company: food and beverage only; not valid toward tax or gratuity; one certificate per table per visit.

• $78 gift certificate (two tickets) to a Rivendell Theatre mainstage show
• 1 platinum ticket to Black Ensemble Theater
• 2 tickets to American Blues Theater
• 2 tickets to Veal by Jojo Jones at A Red Orchid Theatre
• $50 gift card to Rosebud restaurants

Chicago's neighborhood theaters are some of the best in the country, and this package takes you on a tour of four of them.

See a mainstage show at Rivendell Theatre in Edgewater, enjoy a platinum seat at Black Ensemble Theater in Uptown, catch a production at American Blues Theater, and see Veal by Jojo Jones at A Red Orchid Theatre in Old Town. Top off a night in the city with dinner at one of Chicago's classic Rosebud Italian restaurants.

Good to know: Rivendell expires 12/31/2025. Black Ensemble expires 9/30/2026; performance days and times limited. American Blues expires 6/30/2026; book 72 hours in advance; subject to availability; excludes It's a Wonderful Life. A Red Orchid expires 11/9/25.

• 2 tickets to The Second City
• $140 gift certificate to Malarkey Comedy, home of ComedySportz Chicago
• 6 free admission tickets to Zanies Comedy Club (Rosemont)
• $25 Lou Malnati's gift certificate

A whole season of laughs. See the legendary Second City, the stage that launched generations of comedy stars, then check out Malarkey Comedy, home of the competitive improv of ComedySportz Chicago.

Bring the whole group to Zanies in Rosemont with six free admission tickets, and fuel up beforehand with a deep dish from Lou Malnati's.

Good to know: Second City: Tuesday-Thursday and Sunday only; no special performances or New Year's Eve; expires 9/30/26; no one under 13; under 17 must be with an adult. Malarkey expires 12/31/2025. Zanies: reservations required; not valid Saturdays or special events; two-item minimum; $3 service fee per ticket; 21+; valid through 3/2026.

• 2 tickets to Grease at Metropolis Performing Arts Center (Arlington Heights)
• Cooper's Hawk bottle of red wine and 3-month wine club membership for two
• 2 tickets to Oil Lamp Theater (Glenview)
• $100 in Saranello's gift cards (four $25 cards, Wheeling)

Two date nights close to home in the northwest suburbs.

Night one: dinner at Cooper's Hawk and Grease at Metropolis Performing Arts Center, both in Arlington Heights. Your Cooper's Hawk membership keeps the wine coming for three months. Night two: an intimate production at Oil Lamp Theater in Glenview, paired with Italian favorites at Saranello's in Wheeling.

Good to know: Oil Lamp: 2025 season only; expires 12/31/2025. Cooper's Hawk membership: must be 21+; three consecutive months.

• Four-course dinner for 4 with beverage pairings at your choice of Ballyhoo Hospitality restaurant
• Private chef dinner experience for two in your home with Chef Robert Collins
• $100 gift card for a Chicago Food & City Tours walking food tour

For the true food lover. Gather three friends for a four-course dinner with beverage pairings at your choice of Ballyhoo Hospitality's Chicago restaurants.

Then stay in: Chef Robert Collins comes to your home to prepare a private dinner for two, no reservations, no valet, no dishes. Finally, explore Chicago one bite at a time on a walking food tour of your choice.

Good to know: Ballyhoo: valid Sunday-Thursday; excludes tip; expires 11/1/27. Private chef: must be scheduled at least 2 weeks in advance; expires 10/7/25.

• $250 gift card to Pixca Seasonal American Bistro (Highland Park)
• $250 class gift card to The Art Center Highland Park
• Two $50 gift certificates to Noon O Kabab Persian Restaurant (Highwood or Chicago)

Celebrate the hometown that hosts tonight's gala. Enjoy a memorable dinner at Pixca, Highland Park's seasonal American bistro, and discover your creative side with $250 toward classes and workshops at The Art Center Highland Park.

Round it out with two dinners at Noon O Kabab, a Persian favorite with locations in neighboring Highwood and in Chicago.

Good to know: To redeem the Art Center certificate, call 847-432-1888 or stop by the office.