Chicago / Illinois

Signature holes: 2, 7, 13, 14, 18.

Strong play

Cog Hill No. 2 Ravines

Designer: Cog Hill original routing / later improvements
Year: 1929
Par: 72
Yardage: 6,268 yds
Difficulty: Moderate
Green fees: Lower than Dubsdread; public daily-fee rates vary by date/time.

Ravines is the smart Cog Hill companion. It is shorter, more playable, and far less exhausting than Dubsdread. That makes it ideal for arrival day, departure day, or the second half of a Cog Hill 36. If the group wants one facility day without moving bags and cars, this is how you do it.

Strengths

Convenient with Dubsdread
Playable
Good value
Better for mixed groups.

Weaknesses

Not a destination anchor
Less conditioning/pedigree than No. 4
Limited wow factor.

Use it to make Cog Hill logistics work. Sell Dubsdread, enjoy Ravines.

0/5

Signature holes: 3, 8, 12, 17.

Strong play

Harborside International Port

Designer: Dick Nugent
Year: 1995
Par: 72
Yardage: 7,164 yds
Difficulty: Moderate-high
Green fees: Public dynamic rates; verify current green fees direct.

Harborside is the most convenient "city-adjacent" golf play. The Port Course has scale, wind, skyline-adjacent energy, and enough links-ish texture to feel different from the suburban parkland rounds. The caution is current conditioning: call before booking and ask directly about greens and cart-path restrictions. When Harborside is right, it is an excellent downtown-base answer. When it is not, the skyline view cannot putt for you.

Strengths

Close to downtown
Good for city-based trips
36-hole facility
Wind and scale create personality.

Weaknesses

Industrial surroundings are not for everyone
Conditioning can vary by season
Not true links golf.

If you are staying downtown, Harborside should be in the conversation.

0/5

Signature holes: 5, 9, 15, 18.

4.1(317)

11001 S Doty Ave, Chicago, IL 60628, USA

(312) 782-7837

Strong play

Harborside International Starboard

Designer: Dick Nugent
Year: 1995
Par: 72
Yardage: 7,166 yds
Difficulty: Moderate-high
Green fees: Public dynamic rates; verify current green fees direct.

Starboard is the natural Harborside pairing. Most groups do not need both unless they want 36 without changing sites, but that convenience has real value in Chicago. The smarter move is usually Port first, Starboard only if the facility is in good shape and the group wants one easy logistics day.

Strengths

Easy 36-hole day
Close to downtown
Different angles from Port
Good group logistics.

Weaknesses

Similar overall feel to Port
Not essential on a short itinerary
Wind can make the day grind.

Play it with Port if the group wants a clean city-based 36.

0/5

Signature holes: 3, 7, 14, 18.

4.5(685)

2901 W Lake Ave, Glenview, IL 60026, USA

(847) 724-7272

Strong play

The Glen Club

Designer: Tom Fazio
Year: 2001
Par: 72
Yardage: 7,149 yds
Difficulty: Moderate-high
Green fees: Premium public rate; lodging/golf packages may be available.

The Glen Club is the polished North Shore/Fazio play, built on the former Glenview Naval Air Station with enough moved earth to avoid flat-suburb boredom. It has a more upscale feel than most Chicago public golf and works especially well if the group wants to stay on site or avoid downtown chaos.

Strengths

Strong conditioning
Lodging on site
Fazio shaping
Good corporate/group fit.

Weaknesses

Premium pricing
Less gritty personality
Location can be awkward if the rest of the itinerary is southwest.

Excellent if the trip is built north. Annoying if you are forcing it from the wrong base.

0/5

Signature holes: 4, 7, 13, 18.

4.7(1,353)

27W270 Mack Rd, Wheaton, IL 60189, USA

(630) 668-8463

Strong play

Cantigny Golf

Designer: Roger Packard
Year: 1989
Par: 72 by 18-hole combination
Yardage: About 6,900-7,000 yds by rotation
Difficulty: Moderate
Green fees: Public daily-fee rates vary by season and residency/time.

Cantigny is one of the best group-operation facilities in the market: 27 holes, good conditioning, good practice, and enough structure to keep a buddies trip from becoming a spreadsheet disaster. It is not the sexiest name on the board, which is exactly why smart trip captains like it.

Strengths

27-hole flexibility
Strong conditioning
Good group fit
Reliable operation.

Weaknesses

Less famous than Dubsdread
Not a bucket-list course
West-suburban routing required.

One of the safest Chicago golf choices. Not flashy, but smart.

0/5

Signature holes: Depends on rotation; Woodside/Lakeside is usually the strongest first look.

4.8(561)

1700 W Renwick Rd, Romeoville, IL 60446, USA

(815) 254-3333

Strong play

Mistwood Golf Club

Designer: Ray Hearn
Year: 1998
Par: 72
Yardage: 7,005 yds
Difficulty: Moderate-high
Green fees: Public daily-fee rates vary by season and time.

Mistwood is a better golf course than many out-of-towners realize. The renovation sharpened the place, the facility is strong, and the Scottish-ish presentation gives it an identity beyond "another suburb course."

Strengths

Good architecture
Strong clubhouse/practice setup
Good conditioning
Close enough to Cog Hill routing.

Weaknesses

Not nationally famous
Can get windy
Less convenient from downtown than the map makes it look.

Underrated Chicago public play. Use it with Cog Hill or southwest routing.

0/5

Signature holes: 3, 7, 14, 18.

4.5(408)

875 Sports Way, Elgin, IL 60123, USA

(847) 931-5950

Strong play

Highlands of Elgin

Designer: Keith Foster
Year: 2009
Par: 72
Yardage: 7,000 yds
Difficulty: Moderate-high
Green fees: Public/resident and non-resident rates vary by season and time.

Highlands of Elgin is the value-insider pick. It has big land movement, better visuals than expected, and enough quality to justify the drive if the itinerary is northwest/west.

Strengths

Strong value
Dramatic terrain
Good public access
Memorable for the price.

Weaknesses

Far from many bases
Less premium service
Not ideal for a tight itinerary.

Great if routing fits. Do not cross the entire city for it on a short trip.

0/5

Signature holes: 4, 8, 14, 18.

4.4(415)

18231 Park Ave, Homewood, IL 60430, USA

(708) 798-5600

Strong play

Ravisloe Country Club

Designer: Donald Ross renovation influence
Year: 1901
Par: 70
Yardage: 6,321 yds
Difficulty: Moderate
Green fees: Public daily-fee rates vary by date and time.

Ravisloe is the classic-architecture changeup. It is shorter, older, and more charming than most of the modern Chicago public roster. Stronger architecture people will enjoy it; distance-obsessed groups may miss the point.

Strengths

Classic feel
Walkable energy
Good architecture contrast
Public access.

Weaknesses

Shorter yardage
Less premium polish
Not a power-player test.

Use it when the group appreciates old-school golf. Skip it if everyone only asks about yardage.

0/5

Signature holes: 4, 9, 13, 18.

Full course library

Where to stay, eat, and stray

Lodging

Where to stay

Downtown Chicago / River North / West Loop

The Glen Club

Oak Brook / Downers Grove / Lemont suburban base

Dining

Where groups actually eat

Bavette's Bar & Boeuf

Gibsons Bar & Steakhouse

Gene & Georgetti

Things to do

Beyond the golf

Cubs / White Sox game

Best for: Summer groups Our take: Great add-on if the schedule fits. Bad idea if it turns the next morning into a casualty report.

River architecture cruise

Best for: Mixed groups or first-time visitors Our take: The rare tourist thing that is actually worth doing.

Green Mill / Second City

Best for: A Chicago night that is not just another bar Our take: Green Mill gives you jazz history and a proper room. Second City gives you comedy without needing a casino or club. Both beat wandering River North hoping the night invents itself.

Planning mechanics

Logistics

Flights, driving, walking

Flights

O'Hare International Airport (ORD): best for most groups and national flight coverage. Midway International Airport (MDW): useful for Southwest-heavy groups and south/west routing. Chicago Executive / DuPage / Lewis University airports: useful private aviation options depending on course cluster.

Ground transportation

Rental cars are recommended unless staying downtown and playing Harborside only. Traffic should shape tee times. A 45-minute map estimate can become a relationship test.

Walking

Walking policies vary. Carts are common. Caddies are not part of the standard public-access Chicago trip.

Weather

When the trip works best

Spring

Playable but inconsistent; May is better than April.

Summer

Best for city energy, but heat and traffic are heavier.

Fall

September and early October are the premium golf window.

Planning ranges

Cost and value levers

Golf

$$-$$$ - Dubsdread and The Glen are premium public; value exists at Highlands/Ravisloe.

Lodging

$$-$$$$ - Downtown summer weekends can be expensive; suburbs usually control cost.

Dining

$$-$$$$ - Chicago gives you both great splurge meals and casual options.

Itinerary builder

Build your itinerary

The sample on the right is an illustrative Streamsong example.

It is meant to show the depth and shape of a real plan. Build your own around your group, dates, rounds, lodging, dining, and travel timing.

Build my itinerary

Illustrative sample output

Streamsong in 3 Days: 4 Rounds, Mixed Group

3 nights at Streamsong Lodge covering all 3 courses plus a repeat of whichever lands best with the group. With a mixed-skill group and a social thread running through the trip, the sequencing matters: start approachable, build toward bold, and protect evenings for the group to decompress together.

Recommendation

Start with Red to set the right tone for mixed players, not Black. Black's scale can deflate weaker players early and that poisons the rest of the trip.

Day 1

Morning: Arrive, check in to Streamsong Lodge, and get settled without rushing. Arrival timing is unknown, so do not force a same-day round.

Afternoon: If arriving early-to-midday, use the practice facilities to shake off travel; skip forcing an afternoon round on an unknown schedule.

Evening: Make this the nicer dinner night. Gather the group, debrief the plan, and use the evening to build energy for the heavy golf days ahead.

Insider note: Day 1 is the setup day, not a golf day. Burning a round here on travel legs is the most common mistake groups make at Streamsong.

Day 2

Morning: Tee off on Streamsong Red first thing. It is the most balanced course and the right anchor for a mixed-skill group on fresh legs.

Afternoon: Afternoon round on Streamsong Blue. It is more open and wind-affected, which rewards better players while staying manageable enough for the group.

Evening: Keep dinner casual and on property. Two rounds is a full day and the group needs to recover, not power through a production.

Insider note: Red in the morning lets the group settle in before Blue asks harder questions in the afternoon wind.

Day 3

Morning: Play Streamsong Black. Use it as the bold contrast round the guide describes, not as the centerpiece, and set expectations accordingly for higher-handicap players.

Afternoon: Replay the course that resonated most with the group. Red is the likely call for mixed groups, Blue for stronger players who want another look.

Evening: Final evening on property. Keep it relaxed since departure timing is unknown and no one should be grinding through dinner logistics.

Insider note: Black is the experience round, not the best round. Frame it that way for the group before the first tee so no one is quietly disappointed by the rougher edges.

Tradeoffs

Four rounds in two full golf days is aggressive but workable at a comfortable pace. The plan keeps Day 1 golf-free to protect legs and group cohesion rather than chasing a fifth round nobody would enjoy.

Black is scheduled for Day 3 morning rather than being skipped. It adds useful contrast and a memorable moment, but it was deliberately placed after the group already has two courses under its belt rather than as an opener.

The nicer dinner was placed on Day 1 rather than a golf day. This protects energy on the days that matter and gives the group something to build toward without splitting a long golf day around a formal meal.

Book first

Book all four tee times at Streamsong before lodging fills. The property manages its own tee sheet and availability tightens fast in peak season.

Confirm Streamsong Lodge rooms for all three nights in a single block. A small group of 3-4 makes this manageable, but winter weekends can still book out early.

Arrange caddies for at least Red and Blue if the group is open to walking. First-time looks benefit significantly from local knowledge on both courses.

Watchouts

Two rounds on Day 2 is the heaviest ask of the trip. If anyone in the mixed group is a high-handicapper or infrequent player, build in flexibility to skip the afternoon Blue round rather than grinding through it.

Streamsong is genuinely remote and there is no nightlife option off property. Groups expecting energy beyond the lodge bar will be disappointed, and that expectation gap kills trip morale faster than a bad round.

Black's scale and difficulty can frustrate less experienced players, especially after already playing 36 holes the day before. If the group's weakest player struggled on Day 2, consider swapping Black for a Red replay.

LodgingExpand

Overall lodging take: Chicago lodging is a routing decision disguised as a hotel decision. Downtown gives you food and nightlife. Suburbs give you sanity before morning tee times.

City hotel base

Downtown Chicago / River North / West Loop

0/5

Best for: Food-first trips and groups flying into ORD/MDW

Cost: Wide range; events, conferences, and summer weekends can spike.

Pros

Best dining; nightlife; easy rideshare; city energy.

Cons

Parking; traffic; longer morning drives; expensive weekends.

Golf-course lodging

The Glen Club

0/5

Best for: North Shore/Glen Club-focused trips

Cost: Room and golf package rates vary.

4.5(685)(847) 724-7272

2901 W Lake Ave, Glenview, IL 60026, USA

Monday: 11:00 AM – 9:00 PM

Pros

On-site golf; good rooms; easy morning flow; North Shore access.

Cons

Not downtown; not ideal for Cog Hill/Harborside-heavy trips.

Suburban hotel cluster

Oak Brook / Downers Grove / Lemont suburban base

0/5

Best for: Cog Hill, Mistwood, Cantigny, southwest/west routing

Cost: Usually easier than downtown, but event-sensitive.

Pros

Better access to Cog Hill/Cantigny/Mistwood; easier parking; lower costs.

Cons

Weakens the city-dining angle; less memorable.

Rental home

Group rental / suburban house

0/5

Best for: Larger groups prioritizing hang space

Cost: Depends heavily on location and event calendar.

Lodging verdict: For the best Chicago experience, split the logic: downtown for the social night, suburban base for golf-heavy mornings. If you hate moving hotels, pick the identity and accept the tradeoff.

Pros

Common space; cost control; relaxed evenings.

Cons

Location risk; parking and coordination; no hotel service.

DiningExpand

Overall dining take: Chicago is a food city. Use that advantage. One great dinner is the reason to choose Chicago over a quieter golf market.

Steakhouse / main dinner

Bavette's Bar & Boeuf

0/5

Best for: Premium group dinner

4.7(3,957)(312) 624-8154

218 W Kinzie St, Chicago, IL 60654, USA

Monday: 4:00 – 10:30 PM

Classic Chicago steakhouse

Gibsons Bar & Steakhouse

0/5

Best for: Traditional group dinner

4.6(6,760)(312) 266-8999

1028 N Rush St, Chicago, IL 60611, USA

Monday: 11:00 AM – 12:00 AM

Old-school Chicago steakhouse

Gene & Georgetti

0/5

Best for: Groups that want history over scene

4.5(2,237)(312) 527-3718

500 N Franklin St, Chicago, IL 60654, USA

Monday: 11:00 AM – 9:00 PM

Beer, pork, seafood, loud group dinner

The Publican

0/5

Best for: West Loop casual-premium night

4.5(2,956)(312) 733-9555

837 W Fulton Market, Chicago, IL 60607, USA

Monday: 11:00 AM – 2:00 PM, 4:00 – 9:00 PM

Casual/iconic

Au Cheval

0/5

Best for: Smaller groups or off-night food hit

4.7(6,264)(646) 350-2429

33 Cortlandt Alley, New York, NY 10013, USA

Monday: 5:00 – 10:30 PM

Casual group dinner

Green Street Smoked Meats

0/5

Best for: West Loop group meal

4.7(5,093)(312) 754-0431

112 N Green St, Chicago, IL 60607, USA

Monday: 11:00 AM – 10:30 PM

Chicago credential / lunch

Al's Italian Beef

0/5

Best for: Arrival lunch or post-round grab

4.5(3,240)(312) 943-3222

548 N Wells St, Chicago, IL 60654, USA

Monday: 10:30 AM – 12:00 AM

Dining verdict: Book one serious dinner. Keep the other nights flexible by where the group actually finishes golf, not where the spreadsheet wanted them to be.