Best season
Summer-Fall
Jun · Jul · Sep
Trip cost · per golfer
$1,500–$5,300
3-night trip
Nearest airport
ORD
17 mi · ORD
Difficulty
championship
Handicap 5–25
Overview
Chicago offers a surprising array of championship golf just outside the bustling city, blending classic designs with world-class dining and sophisticated urban entertainment for an unforgettable golf escape.
Top courses
Editor-picked layouts ranked by prestige, conditioning and player experience.
Design by Dick Wilson, Rees Jones (renovation) · Par 72 · 7,554 yds
A historic, challenging course known for its PGA Tour heritage and demanding layout. Play from the appropriate tees; Dubsdread is notoriously tough but incredibly rewarding.
Design by Roger Packard · Par 72 · 7,200 yds
An immaculately maintained public course with scenic views and strategic bunkering. Take advantage of their excellent practice facilities before your round.
Design by Dick Nugent, Ken Killian · Par 72 · 7,320 yds
Host of the 1989 PGA Championship, this course features mature trees and numerous water hazards. The course can play long, so ensure your club selection is precise on approach shots.
Design by Dick Nugent · Par 72 · 7,164 yds
A links-style course offering dramatic skyline views and challenging fescue-lined fairways. Don't be fooled by the flat terrain; the wind off Lake Michigan can dramatically alter your shots.
Stay & play
Resort packages bundle lodging, rounds, range access, and on-site dining. Hotel-only options give you flexibility to course-hop.
Luxury Hotel
A luxurious riverside hotel offering sophisticated accommodations and exceptional service.
Mid-range Hotel
A large, centrally located hotel with extensive amenities, perfect for business or leisure.
Boutique Hostel/Hotel
A stylish hostel and hotel hybrid offering affordable, chic rooms and a lively atmosphere.
Ultra-Luxury Hotel
An opulent hotel known for its impeccable service, grand architecture, and prime Magnificent Mile location.
Off the course
Non-golf experiences worth building into your trip — from local landmarks to nature, food, and culture.
Explore Chicago's stunning architecture from the Chicago River on a guided boat tour.
Discover world-class art collections at one of the oldest and largest art museums in the United States.
Visit iconic landmarks like Cloud Gate ('The Bean') and attend free concerts and events.
Enjoy entertainment, dining, and rides with fantastic views of the city skyline and Lake Michigan.
Indulge in upscale retail therapy along Chicago's premier shopping district.
Itineraries
Choose your trip length. Each plan is built around the marquee courses, with rest, dining, and travel days dialed in.
Day 1
Land at ORD, transfer to your hotel, hit the range, and grab a casual dinner at Alinea.
Day 2
Morning tee time at Cog Hill Golf & Country Club (Dubsdread). Lunch at the clubhouse, afternoon recovery, dinner at Lou Malnati's Pizzeria.
Day 3
Early tee time at Harborside International Golf Center (Starboard Course), light lunch, then transfer back to ORD.
Budget
Realistic ranges sourced from current resort rates, public green fees, and group dining averages.
Lodging 3 nights · $214/nt | $642 |
Golf 2 rounds · $125 avg | $250 |
Food & drink ~$110/day | $330 |
Ground transport Rideshare + cart fees | $180 |
Flights Search Skyscanner for live fares | Variable |
| Estimated total · per golfer | $1,402 |
Season
humid continental
When to book: 3-6 months out
Dining
From clubhouse classics to chef-driven dinners worth a reservation.
Progressive American
A three-Michelin-starred restaurant offering an innovative and theatrical dining experience.
New American
A vibrant and popular spot known for its creative small plates and lively atmosphere.
Deep Dish Pizza
Iconic Chicago pizzeria serving classic deep-dish pizzas with a buttery crust.
Steakhouse
A legendary Chicago steakhouse famous for its prime cuts, lively ambiance, and generous portions.
American Fast Food
A beloved local chain offering classic Chicago-style hot dogs, Italian beef, and milkshakes.
Mediterranean
A cozy, wine-focused restaurant serving rustic Mediterranean and Midwestern-inspired dishes.
After dark
Where the buddy trips end up after the 19th hole.
Jazz Club
A historic jazz club with a rich past, offering live music in an intimate setting.
Rooftop Bar
A chic rooftop bar with breathtaking views of Millennium Park and Lake Michigan.
Blues Club
Chicago's legendary blues club, featuring two stages with continuous live blues music.
Tee times
Live inventory from GolfNow plus flight comparison from Skyscanner. Prices update in real time.
FAQ
Summer-Fall (Jun, Jul, Sep). humid continental
Plan on $1,500–$5,300 per golfer for a 3-night trip including lodging, rounds, food and ground transport. Flights are extra.
ORD, about 17 miles from the resort area. Most national hubs offer non-stop service via ORD.
3 nights is the sweet spot — enough for 2 full rounds plus a rest or sightseeing day.
Yes — popular with solo, corporate. Quieter evenings, ideal for golf-focused groups.
Ready to book
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Trip snapshot
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