The Windy City has a special place in my heart. The views, the people and, of course, the food make it an awesome stop for a weekend trip. It’s the perfect compromise; you get the big city but with a Midwest vibe and more green space. With so many things to do, you really don’t have to break the bank, and everything is only a short walk or uber ride away. Active fella on a budget? Get excited, because this city is the ideal place for you.


Lincoln Park is a must-see destination because there are a range of activities all across the spectrum. The best way to start your day is with the Green City Farmer’s Market.

It takes place on Wednesdays and Saturdays and is a great option for scoping out local, fresh vendors. You can grab a smoothie or just walk around smelling the organic fruit, eyeing the unique flavors of jam and chatting with the vendors. Plenty of people are simply walking around with their pups and raking in free samples, which begs the question: what is honestly better than puppies and free samples?

Walking distance from the Farmer’s Market is the Lincoln Park Zoo. Even if you aren’t traveling with kids, this one is worth checking out. It’s in a beautiful location, and there is a wide array of animals in unique enclosures. Plus, it’s free, so you don’t feel like you have to stay all day to get your moneys worth. The zoo also offers yoga sessions exclusively for adults.

Not only will you get a great zen workout to start your day, but the zoo is not very crowded early in the day, so you can get a pretty private look around.


Lincoln Park is also home to the beautiful North Avenue beach. The sand feels more like an ocean beach than a lake beach; it’s soft and refined. Not only can you lie by the waves, but there are plenty of activities to try: Kayaking, stand up paddle boarding, jet skiing and more. It’s far from empty on a warm summer weekend, but it’s worth it if you don’t have a beach vacation planned in your near future. 

If you’re in the mood to take in Lincoln Park but don’t feel like walking around, then you have to grab a drink at the J. Parker at the top of Hotel Lincoln.

If you’re here over the weekend, you need to get there close to the time they open, as the best seats are quickly gone. Getting there early is worth it though because you really can’t beat the view. Their menu features only light appetizers and cocktails, so I wouldn’t suggest coming for a meal, but it’s a great way to spend a couple hours. Plus, the cocktails are delicious.

In Lincoln Park and throughout all of Chicago are rentable bikes, and I recommend them as an easy, active way to explore. There are stops for these bikes all over the town, and they are really affordable to rent for the day. The only catch is that you have to check it back into a station every 30 minutes, just to ensure you don’t ride off with it, and there are enough bikes for everyone. This means that it’s ideal for traveling from one part of town to another, walking around a bit and then hitting the road again. I never saw a completely empty station, so I wouldn’t be too concerned about traveling to one and getting stuck. If you’re skeptical, then check out the map. These bikes are honestly everywhere, and you will have no trouble stumbling upon another one in thirty minutes or less.


If you aren’t gifted with sunny skies on your trip to Chicago then Eataly is a great place to explore. Eataly originally started in New York, and it’s relatively new to Chicago. It’s a multi-story indoor Italian superstore with restaurants as well. Wander up to the nutella bar, shop for unique olive oil or sit down and enjoy a cheese plate paired with excellent wine. The shops are very authentic and have some products I’d never seen before. I’d recommend getting your hands on chickpea pasta while you’re there. Anytime pasta can be made healthy it’s a win, and this stuff tastes just like the real thing.

Another great indoor option is seeing a show. Chicago is known for its comedy shows because of the infamous Second City, but iO is a hilarious, cheaper alternative. The Improvised Shakespeare Company is a popular choice, and you really don’t have to be a Shakespeare fan; they just wear peasant outfits and sometimes talk in accents. The show is in a very intimate room, and there are no assigned seats, but there really isn’t a bad one in the place. This was the hardest I’d laughed in awhile, and it was the perfect way to end the busy weekend.


There are plenty of restaurants to choose from, but a must-stop for me is Quartino. Quartino is in an Italian restaurant in River North with tapas style dishes. These small plates are far from small, though; they are just shy of a single entrée size, so for two people, get three dishes and know you’ll have extra. The pancetta wrapped dates stuffed with Gorgonzola and drizzled with honey are truly amazing, and the pasta dishes come with just the right combination of sauce and cheese; it might have been the best simple marinara sauce I’ve ever had. The wine was delicious and affordable as well. Overall, this has to be the best value in Chicago. On dinner for two, you can spend less than 60 bucks and have more than enough food and wine, which is a great deal in a busy city. You shouldn’t have a trouble making a reservation, but I would recommend it over just trying to walk in.

If you’re big on Mexican food, then please try Frontera Grill as well. Chef Rick Bayless started Frontera, and the menu features gourmet Mexican food with truly unique spices. The champagne margarita is a staple and an absolutely killer combination. All of the food tastes really fresh, and the menu changes slightly every week based on what is in season. This place is very popular, so you will need to make a reservation about a week in advance (or even further if you’re going during the holidays.) Also FYI, Frontera is closed on Sunday’s and Monday’s.