Best Golf Courses Near Chicago for a Buddies Trip
Golf

Best Golf Courses Near Chicago for a Buddies Trip

Published February 3, 2026 · Harbor on 23rd

5 top-tier courses within 90 minutes of downtown Chicago — and the lake house where your crew actually wants to wake up.

The golf trip problem every Chicago crew has

You want to play 36 holes across two days with a group of 8–12. You want it to actually feel like a trip — grilling, a fire pit, somewhere that's not a chain hotel — and you want it within driving distance so nobody has to expense flights. The answer most Chicago golfers don't know: Lake Geneva, Wisconsin. Ninety minutes from downtown, five top-tier courses within a 12-mile radius, and an entire resort-town economy built around group stays.

The five courses worth the drive

1. Grand Geneva Resort — The Brute

The flagship championship course at Grand Geneva Resort — long and muscular, with forgiving fairways that still punish tee shots that drift. It's the one your lowest handicap will talk about for weeks. Located on US-12/WI-50, roughly 5 minutes east of downtown Lake Geneva.

2. Grand Geneva Resort — The Highlands

The Brute's Scottish links-style sibling at Grand Geneva, originally designed by Jack Nicklaus and Pete Dye and later redesigned by Bob Cupp. Rolling terrain, fescue roughs, and visual drama you don't expect in southern Wisconsin. Play The Brute in the morning and The Highlands in the afternoon for the full Grand Geneva day.

3. Geneva National — 54 Holes of Palmer, Trevino & Player

Geneva National is three separate 18-hole courses, each designed by a different legend: Arnold Palmer, Gary Player, and Lee Trevino. Most groups play the Palmer course for its signature lakefront holes — it's the consistent favorite on the property. The Hunt Club Steakhouse on-site is surprisingly excellent; don't skip it. Located about 4 miles from Harbor on 23rd.

4. Abbey Springs Golf Course

The under-the-radar favorite. Abbey Springs is a semi-private course in Fontana-on-Geneva Lake with postcard water views on several holes. Tight, tree-lined fairways reward accuracy over power — a satisfying contrast after The Brute. About 5 miles from the house.

5. Hawk's View Golf Club

Hawk's View offers dramatic elevation changes you don't expect in Wisconsin. The championship course (Como Crossings) is the main 18-hole layout; there's also a shorter par-3 course (Barn Hollow) great for a warm-up round or a quick afternoon nine. Located about 8 miles northwest of downtown Lake Geneva.

The weekend format that works

A proven 2-day format for Chicago groups:

Friday

  • 2 PM: leave Chicago
  • 3:30 PM: arrive, grab beers, rack the clubs
  • 4:30 PM: 9 holes at Abbey Springs or Geneva National (pick a shorter course for the opener)
  • 7 PM: cookout at the house, fire pit, cards

Saturday

  • 9 AM: 18 at The Brute
  • 1 PM: lunch in downtown Lake Geneva
  • 2:30 PM: 18 at The Highlands
  • 6 PM: dinner back at the house, fire pit, second wind
  • 10 PM: pool table

Sunday

  • 10 AM: 18 at Geneva National (Palmer)
  • 2 PM: pack, drive, home by dinner

Total: 63 holes, five cooked meals, one fire pit night, zero hotel desks.

Where your crew actually sleeps

The weak link in every golf trip is usually the lodging. A resort hotel means two-per-room and nowhere to hang out after the round. An Airbnb in the wrong spot means an hour of driving between courses.

Harbor on 23rd is a 4-bedroom home designed for this exact trip — sleeps 14 across 4 bedrooms and multiple beds, 5–6 cars in the driveway, a full kitchen and grill for the pre-round breakfast and post-round dinner, a game room with a pool table for the rainy day, and a fire pit for the 19th hole.

Every course on this list is within 15 minutes. See the full Golf Trips page for trip-planning detail or check dates directly.

FAQ

How close are these courses to each other? All five are within about 12 miles of downtown Lake Geneva. You can play any two in one day without driving more than 20 minutes between them.

Best months to book? May through October. Courses open around mid-April and stay playable through late October in a good year. June weekends book out first — plan 2–3 months ahead.

How many people fit at the house? 14 guests, with multiple bedrooms and sleeping arrangements. Most golf groups are 8–12 and have plenty of room.

Ready to Book Your Stay?

Check availability and book directly on Airbnb. Sleeps up to 14 guests.

4.93★ on Airbnb57+ Guest ReviewsAirbnb SuperhostSleeps up to 14