Enter to win a week-long stay on Cathead Bay in a pet-friendly log cabin!

This cozy - and dog-friendly! - three bed/two bath log cabin overlooks Cathead Bay & Lake Michigan and is surrounded by the woods & sand dunes of Leelanau State Park. The cabin sleeps up to eight. This visit needs to be redeemed before October 31, 2026.

Winner will be notified via email by Tuesday, March 31.

If you kicked off 2026 dreaming of travel like I did, it's time to treat yourself to the best luggage out there - Away! It's chic, it's functional, it'll get you compliments at the airport. This package includes: Away's The Softside Bigger Carry-On in Navy Blue (Qty 1); The (Hardshell) Bigger Carry-on in Navy Blue (Qty 1); Set of 4 Navy Blue Packing Cubes.

Pack your Patagonia black hole duffel bag and head to LondonHouse Chicago for the night. While you're in the city, you and your guest can enjoy the arts at a performance from the Chicago Symphony Orchestra during the 2026-2027 season. This package includes: 1-night stay at LondonHouse Chicago; two tickets to a 2026-2027 season show at the Chicago Symphony Orchestra; and a 40L black hole duffel bag in camel from Patagonia.

Channel your inner celebrity with an exclusive night to remember in downtown Chicago. Enjoy a singularly sensational French-Vietnamese dinner at iconic Le Colonial before spending the night at the glitzy Langham Hotel. Paparazzi not included. This package includes: a $150 gift card to Le Colonial; and a 1-night stay in a deluxe guest room with club access for two at the Langham Hotel.

Plan your very own Chicago getaway with a 1-night stay at L7 Chicago by LOTTE Hotel and a $100 gift card to Happy Camper Old Town. Then explore the city with two Go City Chicago 3-Choice Explorer Passes that allow you to choose three attractions - from an architectural boat cruise to museums and Skydeck Chicago. Package includes: 1-Night Stay at L7 Chicago by LOTTE Hotel; $100 Happy Camper Old Town Gift Card; two 3-Choice Explorer Passes from Go City Chicago.

Calling all food lovers: this is your recipe for a great time. Enjoy a 1-night stay at Midtown Hotel, then level up your skills with a Moody's Market cooking class, and display your culinary creations at home with a beautiful handmade maple charcuterie board. Package Includes: 1-Night Stay at Midtown Hotel; Cooking Class at Moody's Market in Avondale (for one); One Handmade 7" x 17.5" Maple Hardwood Charcuterie Board from Jim's Just Board.

Savor Chicago your way with a walking tour of your choice from Chicago Food & City Tours-packed with neighborhood stories and delicious tastings. Then bring the experience home with a bottle of Lail Vineyards' 2022 Welly Cabernet Sauvignon. Package includes: $100 gift card from Chicago Food & City Tours; One Bottle of Lail Vineyards' 2022 Welly Cabernet Sauvignon.

Make an evening of it - explore Chicago's iconic design on a Chicago Architectural Center walking tour, then raise a glass with a Vin Chicago wine tasting for six. Back at home, keep the experience going with a handcrafted cherry hardwood charcuterie board - perfect for serving your next spread. Package includes: Four walking tour passes from the Chicago Architecture Center; a wine-tasting gift certificate for six people from Vin Chicago; and a handmade 8" x 19" Cherry Hardwood Charcuterie Board from Jim's Just Board.