Chicago: Weekend Getaway

The third largest city in the US (by population) is known by a multitude of nicknames- The Windy City, the Second City, the City of Broad Shoulders- and for good reason. There’s a lot to do in Chicago, from cultural gems like the Art Institute to exploring the city’s booming food scene.

If you’re only visiting for a weekend, it’s impossible to do everything, but there are some things that shouldn’t be skipped over. It’s been a while since I’ve been to Chicago, but I’m planning a return trip in the next few months and can’t wait to revisit a few of my favorite places and check out some new restaurants and bars that have popped up since the last time I visited the Windy City.


Interesting Attractions

  • Millennium Park: In Chicago’s South Loop neighborhood, the park is famous for the Cloud Gate structure (aka The Bean). There’s more to the park than a giant reflective structure though, concerts and events are regularly held at the Amphitheater, and the Crown Fountain, twin-50-foot towers project images of people spitting jets of water. All in all, it’s a cool place to walk through if you’re in the area
  • Willis Tower & John Hancock Tower: Each of these buildings compete with each other, and for good reason- the views from the top are extraordinary. I’d recommend going to the Willis Tower during the day, and catching a sunset or seeing the city at night from the John Hancock Tower
    • Willis Tower: Formerly known as the Sears Tower, you take an elevator 103 floors to Skydeck Chicago for views as far as Michigan, Wisconsin and Indiana
    • 360 Chicago: Breathtaking views of the city and Lake Michigan
  • Art Institute of Chicago: You can easily spend an entire day getting lost inside the second largest art museum in the US (second only to the Met), but a half day here will suffice as well if you’ve got other things on your agenda. Self-guided tours are a great way to see some of the museum’s highlights. When you visit, stop by nearby Grant Park and Buckingham Fountain- it’s a beautiful place to walk around or relax for a few minutes with a coffee
  • Lincoln Park Zoo: Open year round, the zoo is one of the best in the country and free to visit
  • Shedd Aquarium: Housing more than 8,000 aquatic animals, this is the largest indoor aquarium in the world. Perfect for an afternoon when the weather isn’t ideal
  • The Beach: Traveling to the Windy City in late spring, summer or early fall? A morning run on the beach or afternoon walk is a must. Montrose Beach is perfect for dog lovers, and Oak Street Beach is easily accessible from the city- a beautiful place to enjoy the juxtaposition of sand and skyline
  • The Magnificent Mile: I’m not a huge fan of shopping, but walking up the northern half of Michigan Avenue can be a fun way to spend an hour or two while you’re exploring the city. Renowned for its shopping, many of the stores and boutiques are high-end. If you get tired of window shopping, you can always check out Navy Pier.
    • Yes, Navy Pier is touristy, but the Ferris Wheel offers great photo ops, as does the pier itself. If you’re traveling with kids, there are plenty of family activities to keep everyone entertained for an evening
  • Architecture Tour: Chicago’s skyline is impressive and seeing it by boat provides a cool perspective. During the ride, your guide will tell you about buildings on the river and explain how Chicago grew into the city it is today. Chicago Architecture Foundation is my favorite tour provider
  • Second City: Specializing in sketch comedy and improv, this theatre has become one of the most influential comedy theaters in the world
  • Logan Square Farmers’ Market: I’ll never say no to a farmers’ market, but the one in Logan Square is one of my favorites, period. Open on Sundays from 10-3, it’s a great place to start the morning, grab coffee and a snack while you stroll the booths and enjoy the live music
  • Shopping in Wicker Park: This trendy neighborhood is packed with vintage shops and boutiques


The food scene in Chicago is booming right now-  a mix of food traditions, high-end restaurants, and interesting ethnic cuisines means great food from around the world in every price range.

Where to Get Coffee

  • Intelligentsia (locations throughout the city): One of the best places for coffee in the city. Intelligentsia is one of my favorite shops in New York and LA, but visiting in Chicago feels a bit more special since it’s the coffee shop’s birthplace
  • The Coffee Studio (Edgewater): Bright, airy space & a great dolce latte
  • Caffe Streets (East Ukrainian Village): Bacon scone and cortado
  • The Wormhole Coffee (Wicker Park): Really cute cafe with great lattes
  • Gaslight Coffee Roasters (Logan Square): Cozy with a great matcha latte
  • Osmium Coffee Bar (Lakeview): Cold brew on draft #PraiseHands
  • Bow Truss Coffee (River North): Great pour over and cold brewed lattes

Where to Brunch / Have Breakfast

  • Wildberry Cafe (The Loop): Red velvet French Toast FTW
  • La Creperie (Lake View): Great savory crepes and half priced bottles of wine on Tuesdays
  • Tavern on Rush (Gold Coast): Breakfast pizzas
  • Tweet (Uptown): Corn arepas & the veggie country benedict get two thumbs up
  • The Bongo Room (South Loop): The seasonal menu shifts throughout the year, but the banana flapjacks and red velvet pancakes are always a must-order
  • Yolk (South Loop): Strawberry OJ & Challah bread French Toast. The red velvet French Toast also gets rave reviews here
  • Chicago Bagel Authority (Lakeview): For those mornings when you just need a bagel sandwich
  • Firecakes (North Side): Espresso doughnut & ice cream doughnut sandwich are both phenom
  • Doughnut Vault (River North): Famous for its hand-crafted old fashioned doughnuts & creative flavors. The PB&J and buttermilk are crowd favorites
  • Do-Rite Donuts (Multiple locations): Old fashioned doughnuts, obsessed with the vanilla bean-glazed
  • Glazed and Infused (Fulton Market): Great doughnuts with rotating flavors
  • Stan’s Donuts and Coffee (Wicker Park): This LA-based shop specializes in dougnuts with fillings, like Nutella and peanut butter
  • Old Fashioned Doughnuts (Roseland): No frills doughnuts and massive apple fritters

Where to Eat

  • Deep dish pizza at Lou Malnati’s or Gino’s East. Every local has their favorite place for deep dish, but these are two of the classics and both excellent in their own right
  • Portiollo’s (River North): Famous Chicago-style hot dogs
  • Longman & Eagle (Logan Square): An inn doubling as a bar and restaurant with excellent range of whiskeys and superb menu
  • Little Goat & the Girl and The Goat (West Town): Modern American cuisine done right in a super cozy atmosphere. Book weeks-ahead if you’re able, both restaurants can become really busy on the weekends and for dinner. If you’re brunching at the Little Goat, the Fat Elvis waffles are killer
  • Big Star (Wicker Park): Tacos, great cocktails and Mexican street food. Note: Cash only
  • Avec (West Loop): Mediterranean inspired small plates
  • The Publican (Fulton Market): Whatever you end up ordering here, start with the fresh oysters
  • Glenn’s Diner (Ravenswood): Huuuuuuge omelettes with fresh veggies
  • GT Fish & Oyster (River North): Try the baja shrimp bruschetta and lobster roll
  • Mana Food Bar (Wicker Park): Excellent vegetarian & vegan options, loved the baked goat cheese, yellow squash pasta and mushroom sliders
  • Butterfly Sushi (West Town): BYOB affordable, but good sushi
  • Cafe Ba-Ba-Reeba (North Side): Awesome tapas bar, def order the bacon-wrapped dates and blood orange sangria
  • Beatrix (North Side): Quinoa cakes & caramel pie

Where to Drink

  • Lost Lake (Logan Square): Tiki bar serving up fun, fruity cocktails
  • Revolution Brewing (Logan Square): Craft beers and bacon fat popcorn
  • Longman & Eagle (Logan Square): The food is great, but so is the whiskey
  • Public House (North Side): Great beer selection
  • RM Champagne Square (West Town): The Seven Strangers cocktail gets a lot of praise, but the wine list is solid here too
  • Old Town Ale House (Old Town): A+ dive bar
  • The Pump Room (Golden Coast): The food and cocktails are both awesome, personally a fan of the ginger margarita
  • Benchmark (Old Town): Sports bar with a rectractable roof
  • Bull & Beer (River North): Great happy hour spot
  • Scofflaw (Logan Square): Craft cocktails and comfy couches
  • The Aviary (Fulton Market): Imaginative cocktails
  • The Whistler (Logan Square): Come here for live music and craft cocktails
  • Broken Shaker (North Side): Tropical cocktails in a unique spot

Where to Have Dessert

  • Jeni’s Splendid (Multiple Locations): All of the flavors rule, but the goat cheese & cheeries is a personal fav
  • Molly’s Cupcakes (Park West): Cookie monster and red velvet cupcakes are my favs
  • Bang Bang Pie Shop (Logan Square): Kick-ass pies and pretty great biscuits
  • Lickity Split (Edgewater): Order the crazy cake concrete, trust me


Extra Know Before You Go Info

  • Getting Around: Take the L, Chicago’s above-ground subway, it’s easy to figure out their transit system and affordable to ride. If you’re flying into Chicago, the subway goes directly to O’Hare and Midway from downtown
  • City Pass: If you plan on visiting a few of Chicago’s top attractions, consider a city pass, like Chicago CityPass or Go! Chicago, which offer discounted admission or skip-the-line access to a number of places, including: Shedd Aquarium, SkyDeck Chicago, The Field Museum, Art Institute of Chicago, etc. Normally, I’m not a huge fan of city passes because I like to see things at my own pace, and often only pick one or two well-known attractions to visit, but we did a city pass on my first trip to Chicago years ago while I was still in college, and it made a world of difference in how much we were able to see and do in a short weekend trip
  • Where to Stay: There are plenty of hotels to choose from, search Hipmunk for good deals if you want to stay downtown. I usually opt to stay in an Airbnb in Wicker Park, Logan Square or the North Side of Chicago

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