




There are few summer destinations in the world better than Chicago. The city hits nearly every desirable bucket — from outdoor activities to food to nightlife — and provides a wonderful atmosphere for almost anything you can imagine. The seeds of a great summer day can be traced back 150 years. After the Great Chicago Fire in 1871, the city got a reboot, and architect Daniel Burnham hatched the marvelous idea to create a wealth of protected lakefront for Chicago residents and tourists. Today, Chicago boasts 28 miles and over 3400 acres of managed open space right on perhaps the world’s greatest lake, Michigan. This open space is filled with beaches, harbors, parkland, a museum campus, a football stadium (for now), and even a few public golf courses. It provides a wonderful buffer of recreational space between where people live and where people can congregate or get away from the hustle and bustle of city life. On top of the lakefront, the city is buzzing with activity during the summer.
As a Chicagoan and a resident of the city for 12 years, it's safe to say Chicago is wired to go during summer, as residents know there is plenty of time to rest in the winter. In this guide, I will attempt to do this great city justice, calling out some of the best public golf courses, neighborhoods, activities, and restaurants that are worth your time if you visit the third coast. Before I get to the specifics, here are some quick thoughts:
Golf Courses: While there are many public golf options, the uncomfortable truth is, none are great. Chicagoans have every right to be proud of their vibrant golf scene, but the naturally flat terrain and the haphazard 1990s-era redesigns can’t measure up to the exceptional public golf options you can find in places like Traverse City or Wisconsin. However, those locales do not offer the wide range of non-golf activities and attractions that the Chicagoland metro offers, which can entice non-golfing travel companions to jump at the chance to visit. The courses listed below are my favorite places to play over a lifetime of being a public golfer in the city.
Where to Stay: My big advice would be: Don’t bother staying downtown. The Loop is central to everything, but doesn’t have a neighborhood feel. Most of the hotels are in River North, Streeterville, and the Gold Coast. These are all pleasant neighborhoods to stay in, close to shopping, the beach, and some great restaurants. You’ll find neighborhoods with less touristy vibes below.
Activities: There is so much to do in the summer in Chicago, it can feel hard to narrow it down, but I did my best. One thing I cannot recommend under any circumstances is going to Navy Pier. To be blunt, it sucks.
Where to Eat and Drink: This could be a guide unto itself. In order to keep this brief, I only included my very favorite locales. There are a lot of websites and publications you can seek out for dinner and food recommendations; I personally really like The Infatuation.
Before we get to all of my recommendations, this is a living document, so please let me know what you think or what we may have missed! Chicago is a massive city with so much to offer, and as Frank Sinatra once sang, it’s the one town that won’t let you down.
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This area exploded in the 2010s and offers a spectacular restaurant, shopping, and nightlife scene. Just about any itch you have, you can scratch here. For golf, it’s conveniently right off the highway, offering the ability to go North, South, or West, something that virtually no other neighborhood offers. The one downside is it’s a hike from the beach and doesn’t have that classic Chicago neighborhood feel.

This is my personal favorite area of Chicago. While it is a bit of a hike from the waterfront, it makes up for it with its food and nightlife. This area has its own individuality and vibrancy that sets it apart from the rest of the city. Logan Square is an adversary to the West Loop. Its proximity to the highway makes for easy access to the golf courses north of Chicago.

If you want the classic gold standard Chicago neighborhood with the ability to explore the lakefront, look no further. Lincoln Park is a beautiful place and has a growing restaurant scene. While it’s inconvenient to golf anywhere but north of the city, it offers a great mix of outdoors and nightlife activities and proximity to Wrigley Field.

If you are visiting family or friends who live in the suburbs, there is no shame in staying there. It’s fine and I will include some food recommendations out in the ‘burbs. These places don’t have the attractions and food that Chicago offers, but they are much closer to golf.

The best ballpark in Major League Baseball and the best place to spend a Friday afternoon in the city. If you are a baseball fan, a trip here is a must. The Cubs operate a very nice hotel, Zachary, next door to the stadium that is pricey, but it can include tickets to a game.

Chicago is home to some of the best architecture in the world. The buildings are stunning. This boat tour takes you up and down the Chicago River and educates you on the history of the city. Even locals enjoy taking the tour multiple times.

If you are from either coast of the U.S., you won’t believe how wonderful the Great Lakes are. They are warm, have fresh water, and you don’t have to fear that anything in them will sting or attempt to eat you. The beaches are a great place to hang out for a few hours on a summer day, especially if you’re with kids. North Avenue Beach has a bar called Castaways that’s a fun place to down some drinks. Oak Street Beach is the easiest one to get to from most of the hotels. Montrose is a dog-friendly beach, but it’s also wonderful even if you don’t have a dog.

All summer long, every weekend, there is a different neighborhood street festival. This is a great way to go out and experience the different flavors that each neighborhood in Chicago has to offer.

I am a golf writer, writing about why I might go visit one of the best aquariums in the world but … it’s rad! Also, it’s even more likely to make your itinerary if you have kids, like I do.

Maybe a place I wouldn’t bring a toddler or young child, but I enjoy looking at art and pondering its meaning. The Art Institute is one of the best places to do that.

This is a great spot to spend a morning walking around. The Bean, even if it is influencer catnip, is really cool.

A free zoo in one of the country’s finest city parks. Do I need to explain further? It’s fun to just wander through here during the day.

For biking and running enthusiasts, this is a great place to log some miles. A particular favorite of mine is if you are staying in the hotel district, go for a run and then jump in the lake off the seadeck just north of Oak Street Beach. It’s the best way to cool down before walking back to your hotel. A lot of people make fun of the concrete steps, but we have a ton of beaches and this is a place where you can just jump right into deep water. Remember, variety is the spice of life.

If you are staying in the Wicker Park/Bucktown or Logan Square area, the 606 Trail is a great place to run.

This is a big-time shopping attraction where you can find virtually any store.

If you are traveling with kids, this is a monster and awesome park for them to burn off energy.

There is a wide range of outdoor concerts that run all summer long. Obviously, in early August you have Lollapalooza, but it's worth checking out the schedules at Northerly Island, The Salt Shed, Soldier Field and Millennium Park.

One of two restaurants owned by Fried Egg Chicago Guide video star David Posey and his wife, Anna, Elske earned a Michelin star for its inventive Scandinavian cuisine in Chicago’s West Loop.

The Poseys’ second restaurant is not to be overshadowed by Elske. This French-inspired cuisine is to die for. With both restaurants, dessert is not to be missed, as Anna Posey is widely known as one of the best pastry chefs in the world.

Chicago is filled with great steakhouses, and this is my favorite.

Why would someone from Chicago recommend a pizza place that didn’t serve Chicago-style pizza? Because coal-fired pizza is excellent, and this is one of my favorite establishments.

The best deep dish pizza in Chicago thanks to its caramelized crust. It has only one location in the city, and wait times can be long, so the trick is to put your name in and visit one of the nearby watering holes. If you are looking for Tavern Style, I would go elsewhere. There is another Pequod’s location in the Northern Suburbs in Morton Grove.

A relatively new tavern style pizza place in the great food corner of West Town. Their pizza is off-the-charts good, but all the appetizers and salads were spectacular, as well. The owners of Pizza “Mici also own a small pizza shop in the western suburbs called Kim’s Uncle.

Listen, getting to one of the local pizza shops can be hard depending on where you’re staying. Lou Malnati’s has locations everywhere and they have very good deep dish and tavern style pizza if you want both. Order your pizza uncut if you have access to a pizza cutter.

An ideal pairing after a round at Ravisloe (or Beverly, if you are lucky), this southside institution has the most famous tavern style pizza in the city. It’s cash only. Enjoy a nice pint of Old Style with your pie.

One of the must-visits of the West Loop, Monteverde is the premier Italian restaurant in the city. Reservations are tough to come by, so try to book early.

If you are looking for no-frills Italian in a neat little pocket of Chicago, this West Town staple is one of my favorite places to eat.

Close to a lot of the big-time hotels in Chicago, this bar has large booths, interesting pizza options, and excellent gnocchi.

My favorite tacos in Chicago. There is a lot of great food and Mexican options around it as well.

An awesome bar with really good food in Bridgeport; ideal to pair with a White Sox game.

A famed Chicago establishment that was featured in “The Dark Knight.” The ribs here are delightful, and it's a particularly cozy place to go in the fall.

Breakfast, lunch, or dinner, this is one of the institutions that put Logan Square dining on the map. One of the saddest things about moving out of Logan Square was losing the proximity to this restaurant.

This is my favorite restaurant in Lincoln Park; they do a four-course menu of Middle Eastern fare. Don’t skip the carrots.

This restaurant has been around for almost 20 years and has remained among the very best in Chicago. Avec serves out-of-this-world Mediterranean cuisine.

Fantastic bar with great bar food. Close to the main hotel district of Chicago. Like others on this list, a tough reservation to get.

This West Loop bar topped Bon Appétit’s list for “Best Burger in America.” The fame has created long waits for tables, but it’s the rare spot that’s worth it. The food is to die for. The nice thing about the wait is there are plenty of bar options to bide your time. Try Lone Wolf Tavern down the street.

For a sit-down restaurant, this might be my favorite burger in Chicago. It’s a worthy adversary to Au Cheval.

On a nice summer day, this is a wonderful place to have some casual fare and down some refreshments on the west side of town.

One underappreciated aspect of Chicago cuisine is our Italian delis and sandwiches. Bari is my favorite of the quartet that includes JP Graziano, Vinnie’s Subs, and Conte Di Savoia, but I would recommend trying them all if you have time to formulate your own opinion.

Some of the best tacos in the Bucktown, Wicker Park, Logan Square orbit.

This has become the most famous Italian Beef spot in Chicago thanks primarily to its depiction on the hit TV show “The Bear.” Expect lines, but it is one of — if not the best — beef within city limits and convenient to most hotels.

This is probably the most widely thought of “best beef” in Chicago, but it is in Elmwood Park outside of the city limits.

The success of this original Taylor Street location launched a chain of Al’s Beefs around the city. The original is the place to go as they still make all their ingredients from scratch.

There are a ton of locations around the city and while they aren’t quite as good as Au Cheval, they do offer a really strong burger that is far more convenient and quick than trying to get one from their main restaurant.

Great hot dogs and smash burgers here. They have a couple of locations, including one in Skokie, which is easy to hit on your way back from Canal Shores or Sunset Valley.

The same owners as Redhot Ranch, this hot dog stand makes waves for their social media efforts.

This place was an early adopter of the craft coffee scene and gives you a wonderful snapshot into the old feel and vibe of Wicker Park.

Much like Lou Malnati’s, it can be hard to get into some of these independent restaurants. Portillo’s does a nice job with its Italian beef and Chicago-style hot dogs, and there are locations everywhere across the Chicago suburbs.

My most recent addition to my Chicago recommendations. This casual Wicker Park establishment serves up wonderful Bahn Mi’s.

Another star of the Chicago Guide Video, Danny Shapiro was one of the visionaries of the Chicago mixology scene. Although he and his team have gone on to open several popular bars, his original effort in the Ukrainian Village remains one of the best spots in the city to have a delightful cocktail.

The most recent addition to the portfolio of Shapiro and his team, this craft cocktail bar in Humboldt Park is one of the most talked-about recent openings.

A cocktail bar mainstay of the popular River North area with delicious drinks and a wide-ranging selection.

Looking for a casual bar to pass some time? This is one of my favorites in the city and a great place to meet before or after a meal in the West Loop.

One of my favorite cocktail bars on the west side.

The home of the Shotgun Start’s infamous “Lotte at Lottie’s Challenge.” Lottie’s is not going to knock your socks off with drinks. It’s more of a dive than a cocktail bar. But it’s a quintessential Chicago neighborhood bar.

Where else can you take batting practice before a Cubs game? The other Wrigleyville bars I’d recommend are Murphy’s or Bernie's.

A no-frills, Lincoln Park neighborhood bar, which I refer to as the Blurwood.

If you enjoy late-night live music, this is your spot. This blues bar is a wonderful place to close out a night.

A wonderful, cash-only jazz club on the far north side of Chicago.





This Donald Ross design on the Southside is a former country club and offers the best walk in Chicago. The golf course features a severe set of greens and a nice bit of topography (particularly for Chicagoland) on the back nine. Unfortunately, over the past decade, the course’s approach to managing the property by planting hundreds of trees and not investing in modern agronomic practices. Despite the declining product, it’s one of the finest courses in the area and easy to get to from the city.





This longtime municipal course was reimagined by Dave Esler as an ode to the greatest examples of golf architecture in Chicago. Seth Raynor designed Chicago Golf Club and Shoreacres — two of the best courses in the country — and Esler decided to bring Raynor’s “templates” to the public. At Mt. Prospect, you can play renditions of the Redan, Biarritz, Double Plateau, and others. Like most popular public golf courses, it can get busy and slow here in the afternoons.

One of two good courses in Elgin, this Keith Foster redesign is one of the best values in Chicagoland. It’s a hike from the city, but there is good, fun golf here that won’t break the bank. If you can only play one course in Elgin, Highlands would be my pick.





The other quality golf course in Elgin boasts slightly better conditioning, but that comes with a slightly more expensive greens fee. One of the cool aspects of Bowes Creek is its model. You’re allowed to play as much golf as you want for the green fee, usually around $100 depending on what time of year and day of the week you visit.



The most convenient course for those staying in the city and an idyllic setting for golf, it’s right on Lake Michigan. There is one caveat: I will only play this golf course within the first hour of the day. I will reiterate, I do not recommend playing this course at any other time due to pace of play. Also, do not expect country club conditioning or extraordinary architecture; you are there to get in a quick nine while staring at Lake Michigan.





Rick Jacobsen did a really nice job reimagining this tired, flood-riddled municipal golf course. While Jacobsen’s heavy-handed shaping can be a bit much, there are some fun greens and clever golf holes on an uninspiring piece of land. For the price and conditioning, this is a really good value in Chicago.

For decades, Canal Shores (once known as Peter Jans) toiled in disrepair. But in 2022, Kemper Sports took over the community course and poured money into it, with Todd Quinto leading a full renovation of the quirky property. Reimagining all 18 greens, Quinto has infused a lot of interest into a very difficult site. Today, Canal Shores stands as one of the most unique places to play golf in America. You cross roads, go under the EL, and are right in the heart of the hustle and bustle of Evanston. It’s accessible from the city with both a Metra and Purple Line stop within walking distance. With an outdoor bar and giant putting green, this is also a fun place to hang out in the afternoons. You won’t hit a lot of drivers, but you will see a bunch of stuff you don’t see at most courses in America.

During my glory years looping along the North Shore of Chicago, the Crook was a mainstay for our caddie money games. Built on a landfill, it’s one of Keith Foster’s early designs, and is a really fun track at a good price. There are, however, a couple of downsides: It can smell really bad when the wind blows the wrong direction, and it can be a bit slow.





This golf course is not my cup of tea. If I were hosting clients, or on a work trip where people expected country club-level conditioning, this is where I would play. That being said, it’s one of the worst values in all of golf.