5 Best Group Golf Trips from Chicago for 2026

Chicago golfers are spoiled for choice. Fly south to the Caribbean, west to the Arizona desert, east to the Carolina coast, or over the Atlantic to the historic links of Scotland and Ireland. But with so many great destinations, the question becomes: which one is right for your group this year? At Sun & Fun Travels, we have spent years planning group golf trips for Chicago-area golfers — buddy trips, country club outings, corporate events, and bachelor parties. Based on what we are seeing in 2026 — booking trends, course availability, resort value, and sheer experience quality — here are the five destinations we are recommending most strongly.

1. Jamaica — The All-In-One Golf & Resort Experience

Jamaica is our single most popular group golf destination for Chicago travelers, and 2026 is as strong as ever. Sandals Golf & Country Club in Ocho Rios is the marquee layout — a challenging 6,900-yard course set in the lush Blue Mountains, with spectacular scenery and a world-class Sandals resort attached. Cinnamon Hill Golf Course in Montego Bay is another strong option, particularly if your group is staying at Sandals Montego Bay.

The all-inclusive model is what makes Jamaica work so well for groups. One price covers accommodations, all food, all drinks, and most activities. No splitting bills, no managing a group budget on the fly. Your group organizer can focus on enjoying the trip rather than administering it. Fly time from O'Hare to Montego Bay (MBJ) is approximately 3.5 hours, with direct flights available most days. Best travel window: January through April.

2. Scottsdale, Arizona — Desert Golf at Its Peak

For Chicago groups who want world-class golf without a passport, Scottsdale is the answer. TPC Scottsdale (host of the WM Phoenix Open), Troon North, Whisper Rock, Grayhawk, and Quintero — the destination is home to an embarrassment of riches in terms of elite course options. The desert landscape creates a visually dramatic backdrop unlike anything you'll find in the Midwest, with red rock formations and saguaro cacti framing fairways at every turn.

Phoenix Sky Harbor is a 25-minute drive from most resorts, with multiple direct flights daily from both O'Hare and Midway. Best travel window: October through early May.

3. Myrtle Beach — Best Value, Best Variety

If your group's priority is maximizing rounds played per dollar spent, Myrtle Beach wins every time. The Grand Strand has over 100 golf courses — from budget-friendly layouts to true gems like Caledonia Golf & Fish Club, True Blue, and TPC Myrtle Beach. You can play three premium rounds for roughly what one round costs at a top Scottsdale venue, making it the perennial champion of value-conscious group trips.

Myrtle Beach stay-and-play packages are purpose-built for groups and we negotiate directly with resorts and courses to get the best combination for your group. Drive-in from the Chicago area or catch a direct flight — either way, arrival logistics are straightforward and the weather is reliable from March through November.

4. Dominican Republic — Casa de Campo & Teeth of the Dog

For serious golfers who want a bucket-list experience combined with a luxury resort stay, Casa de Campo in the Dominican Republic deserves to be on the short list. The Teeth of the Dog course — designed by Pete Dye — is consistently ranked among the top 25 courses in the world, with seven holes directly on the Caribbean Sea. Playing this course once genuinely changes how golfers describe their best-ever rounds.

The resort infrastructure at Casa de Campo is outstanding — multiple other courses on property, clay court tennis, polo, shooting range, and a private beach village. Best travel window: November through April.

5. Scotland — The Pilgrimage Every Golfer Needs to Make

Scotland is not just a golf trip. It is a pilgrimage. St Andrews Old Course, where the game was born. Carnoustie, the toughest major venue in the Open rota. Royal Troon, Turnberry, Kingsbarns — each one a living piece of golf history that no Scottsdale resort or Caribbean beach can replicate. Walking the 18th fairway toward the Swilcan Bridge at St Andrews is a moment that stays with golfers for the rest of their lives.

We have planned Scotland golf trips for Chicago groups ranging from 6 to 30 players. Every client says the same thing afterward: worth every penny, worth every mile.

Ready to Plan Your 2026 Group Golf Trip?

Every group is different — different budgets, different skill levels, different priorities. Call Pete at 815-409-2705 or visit our Group Golf Trips page to start the conversation. We will find your perfect destination and handle every detail so your group can focus entirely on the golf.