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The Chicago One-Two Punch Guide: Summer Edition

9 two-step plans that are perfect for summer.

Written by
18 Spots
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18 Spots
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The One-Two Punch is our two-stop itinerary for maximum fun. We've already given you our best one-two punch options for date night, and now we're back at it again with another round.

What you'll find here are two-step plans that are perfect for summer, whether you're looking for actual activities or simply to eat and drink. Use these combinations for date nights, group hangs, entertaining out-of-town visitors, or to be a tourist in your own city instead of always being lazy. You can do it.

The One-two punches

Architecture Boat Tour

$$$$ Chicago River

You have friends in town, they want to do something really “Chicago,” but you don’t feel like being that interesting of a host. Hit up the architecture boat tour and your problem is solved. It’s the one touristy thing that everyone who lives here should do at least once a summer because it reminds you how great this city is, especially when it's nice outside. Then pretend it's always nice outside.

The Purple Pig

$$$$ 500 N Michigan Ave

Post boat tour, keep the touristy yet enjoyable theme alive by heading to The Purple Pig - the one restaurant on Michigan Avenue that doesn’t make us want to kill ourselves. They don’t take reservations and there’s probably going to be a wait, but you won’t mind because there’s plenty of space on their walkway to hang out and have a drink. Your friends will be impressed and you’ll actually have a great day.

Bistro Campagne

$$$$ 4518 N Lincoln Ave

It’s summer, it’s beautiful outside, and you have a special someone you want to take to dinner. Don’t f*ck it up. An easy way for a romantic evening is a weekend date night at Bistro Campagne. This Lincoln Square French restaurant has great food and a quaint patio, which is how we like all of our French restaurant patios to be.


$$$$ 1970 W Montrose Ave

Dinner went well and now you want to get a little loose. Not "dancing" loose, because you suck at that, but at least loosen up the conversation a bit. Walk a few blocks to Fountainhead where they have an excellent rooftop great for drinks. A couple of those and you'll be convinced you're a good dancer, even though you're still not.

Museum of Science and Industry

$$$$ 5700 S Lake Shore Dr

Here’s a friendly reminder that Hyde Park does not have cooties. You are allowed to go hang out there and we promise it will be fun. A good start is a visit to the Museum of Science and Industry. “But I don’t like museums, they’re educational,” you say. Ya, but this museum has hands on experiences plus an exhibit where you can watch baby chickens hatch, and that's bound to put a smile on your face.

Medici on 57th

AmericanBurgersPizza  in  Hyde Park
$$$$ 1327 E. 57th St.

After learning about science, treat yourself to the greatest scientific accomplishment this world has ever seen - pizza. Medici is the classic neighborhood pizza, burger, and sandwich joint in Hyde Park, and not many places are more comfortable and welcoming to hang.

The Duck Inn

$$$$ 2701 S. Eleanor St.

Head to Bridgeport for one of the best one-two eating and drinking punches of all-time. Start at The Duck Inn, a great restaurant for dinner throughout the week or lunch and brunch on the weekends. If it’s nice out, hit their patio, and then wonder why you don’t go there to eat more often.



$$$$ 960 W 31st St

Next up is Kimski, a 10 minute walk away, which is the fancy new split personality to Maria’s Community Bar. If you’re unfamiliar with Maria’s, it’s been the neighborhood favorite liquor store and tavern hybrid in Bridgeport for a long time. But they recently bought out the space next door and turned it into Kimski, a Korean-Polish restaurant and bar that’s much more modern-industrial looking with a nice little patio out back. Sound like a lot going on? It is. But trust us this is the perfect place to have a few drinks, plus maybe some poutine if you get hungry again.

Kaiser Tiger

$$$$ 1415 W Randolph St

Beers, bacon, and bocce ball make for the perfect afternoon. Gather up a few friends and head to Kaiser Tiger where you can do exactly that. The patio is enormous so feel free to bring a few extra friends or friends of friends if you want.

Forno Rosso

AmericanPizza  in  West Loop
$$$$ 1048 Randolph Street

An afternoon of drinking and games will inevitably build up an appetite. Grab some snacks at Kaiser Tiger if you want, but don’t overdo it there. Once you're hungry enough that you've contemplated eating an actual bocce ball, walk down the street to Forno Rosso for pizza. Their Neapolitan-style pies are some of the best around.

Lincoln Park Zoo

$$$$ 2001 N Clark St

You’re an emotionless robot if you don’t like going to the zoo, especially a free one that doesn’t cost an exorbitant amount of money to check out. The Lincoln Park Zoo is basically an extension of the park, so take a walk through both and figure out which animal you want to be in your next life. Animals are so much better than people anyway.

The J. Parker

$$$$ 1816 N Clark St Fl 13

Even though animals are better than people, being a person having cocktails on a rooftop overlooking Lake Michigan is still pretty cool. The J Parker at The Hotel Lincoln is across the street from the park and the zoo complete with one of the best rooftops in the city. You’re basically a drunk bird while you’re up there.

The 606 Trail

$$$$ 1751 N California Ave

If you don't have an ex-railway that's been shut down and turned into a public walking space, can you even call yourself a city? Your New York friends visiting will be all "OMG this is like the High line I love the High Line." That's annoying, but the 606 trail is not. The walkway mostly cuts through Wicker Park, Humboldt Park, and Logan Square, and makes for a great walk, run, or ride on wheels of sorts during the day.

Bang Bang Pie & Biscuits

$$$$ 2051 N California Ave

There are two things we love about walking along the 606 trail. One - it's nice. And two - you can then tell yourself you burned some calories and use it as an excuse to hit up Bang Bang Pie. Hop off the 606 at the California Ave. access point and walk three blocks north to Bang Bang. Eat biscuit sandwiches and eat a bunch of pie before deciding you should maybe walk it all off.


$$$$ 111 W. Hubbard St.

The key to any successful nice dinner out is to have a drink beforehand. And seeing as River North is full of great restaurants, you should start at Celeste for a cocktail on their roof. It's a very lounge like vibe, and a particularly good place to start for any summer date night outing.

Gilt Bar

Gilt Bar

$$$$ 230 W Kinzie St

You've had a cocktail or two and now you're ready for dinner. Gilt Bar is around the corner from Celeste and is a strong move for a decadent dinner of pastas, steaks, and sides. Get a patio seat if you're not sweating from the heat, but sitting inside is an acceptable choice either way. The lighting makes you feel like you stepped onto the set of a Rihanna music video, which is a light setting we want available in our homes.

Emporium Arcade Bar

$$$$ 2363 N Milwaukee Ave

You're never too old for video games, which is why we can't hate on Emporium. The minute you get sucked into classic pinball or Centipede you remember why it's all so addicting. Drink alcohol and play arcade game with your friends because that's what 10 year old you would have wanted the future to look like.

Small Cheval

$$$$ 1732 N Milwaukee Ave

Once you beat Mortal Kombat and claim yourself champion of the realm, you're going to need a celebratory meal. Don't bother waiting for a table at Big Star. Instead, head a few blocks further north down Milwaukee and grab burgers and beers and Small Cheval. There's unlikely to be a wait and they also have a nice patio to sit outside.

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