You can get a downloadable map of this itinerary here.

***Written by Chicago local, Christina. Born in Indiana and raised in Georgia, Christina loves that Chicago combines the inviting and good-hearted nature of the Midwest with the hustle and bustle of a big city. She’s lived on the north side for 2 years and continues to explore the diverse neighborhoods this city has to offer.

BEST TIME TO TRAVEL: The prime time to visit Chicago is between May and October (unless of course you just REALLY love blistering winds and lots of snow). Keep in mind July and August can get a bit hot with humidity being a factor, while May and October are a little more unpredictable in terms of temperature and rainfall. 

PLACES TO STAY: If you’re looking for a room with a view, search along the east branch of the Chicago River (the portion that runs east/west through downtown). You can’t really go wrong with any of these hotels, but some personal favorites are LondonHouse or The Langham if you’re looking to splurge a little. Hotels in the River North/Magnificent Mile area also put you in a prime spot to explore the city. If you’re a night owl or want to stay in a trendier neighborhood, check out Fulton Market – I recommend The Hoxton or Nobu Hotel! You’ll find a handful of hotels in The Loop, but I would avoid staying in this area as a tourist; The Loop is primarily home to business offices and pretty dead once the sun sets.

friday.

Once you get settled into your hotel, head down to the riverwalk for one of the city’s most iconic activities – an architecture boat tour. This is one of my absolute favorite ways to see the city! These tours take you down the Chicago River and into Lake Michigan, while your tour guide will share interesting facts and stories about the history and architecture of Chicago. Get your tickets from Shoreline Sightseeing or Wendella. 

When I first heard about the architecture tours, I thought (and maybe you are too) – How in the world will I not be bored listening about architecture for 90 minutes?? But TRUST ME. The tours are so intriguing and each guide has their own unique delivery, so even if you come back a second time, you’ll always learn something new. I think the cruise is best done at sunset so you’ll get incredible photos of the skyline, but tours are offered all throughout the day. 

Once it’s time for dinner, head on over to River North for countless delicious options – try Quartino Ristorante, Italian small plates and Neapolitan pizza with an extensive wine list; Bar Goa, Indian-Portuguese fusion; or avec, a stylish Mediterranean-inspired spot. 

If you prefer something a little more greasy, head on over to Portillo’s for a classic Chicago dog or Italian beef sandwich. And don’t miss their Chocolate Cake Shake, which is (if you can believe it) a milkshake blended with a full slice of their ultra-famous chocolate cake. 

After dinner, you’re a short walk away from some awesome cocktail bars. My favorite is The Berkshire Room, which offers a “Dealer’s Choice” cocktail – you select your booze of choice and flavor profile, and the bartender will whip up something unique and special for you. The drinks never disappoint, and it’s a fun way to get out of your cocktail comfort zone! If you’re looking to hop around, also check out Three Dots and a Dash, a tucked-away tiki bar with tropical rum drinks; Celeste, an upscale club where each of the four floors offers a different style and experience; or Untitled Supper Club, an expansive bar and restaurant with frequent live entertainment. 

saturday.

Wake up and head on over to the Doughnut Vault for a cup of coffee and one of their famous Old Fashioned. If you’re looking for a more substantial start to the day, check out brunch at Beatrix, an American restaurant with lighter fare; Land & Lake Kitchen, featuring a classic brunch menu with a great bottomless mimosa deal; or Venteux, a sleek French bistro with unmatched ambiance. 

Once you’re fueled up, take your pick of one of Chicago’s spectacular museums. There are truly SO MANY to choose from, and you can’t go wrong – it just comes down to your personal interests. Consider the Field Museum, Shedd Aquarium (my go-to), Chicago History Museum, Museum of Contemporary Art, Museum of Science and Industry, The Art Institute, the list goes on! Most of these options will take at least 2 to 3 hours to go through, but you can definitely spend even more time at the larger ones like Field Museum and Museum of Science and Industry. 

I would be remiss if I didn’t at least mention Navy Pier. As you can probably imagine, it’s a huge tourist trap with overpriced food, drinks, and gift shops. Entry to the pier itself is free, so if you’re just looking to take in some sights of the city and water (and maybe even hop on the Ferris wheel), then it’s a nice stroll! But I would recommend spending your money elsewhere. 

After the museum, take a walk through Millennium Park (home of Cloud Gate aka the Bean), Grant Park, or Northerly Island. One of my favorite parts of the city, the Buckingham Fountain, is a gorgeous display and is typically open from early May through mid-October (the exact dates depend each year on the weather, so make sure to do a quick Google search if you’re visiting around those times). 

You can’t visit Chicago without gorging yourself on some deep dish, so try this out for lunch! The pizza itself takes around 45 minutes to bake, so if you go for dinner, you’ll likely have a much longer wait. While the debate about who has the best deep dish pizza in the city will last until the end of time, my personal favorite is Giordano’s Chicken Sausage Deluxe with spinach and mushrooms. Other popular spots are Lou Malnati’s, Pequod’s, Gino’s East, and Pizzeria Uno (technically the original deep dish), but plenty of restaurants around the city offer this famous dish. 

Once you’ve finished lunch, take a walk around Magnificent Mile, the city’s popular shopping district. Even if you’re not into shopping, it’s a cool stretch of the city to take in, and a lot of popular shops take up massive amounts of real estate. You’ll also pass by historic markers like the Wrigley Building, Tribune Tower, and Historic Water Tower! 

For dinner, it’s time to head over to the west side. Chicago is home to a bunch of incredible restaurant groups, one of which is called Goat Group. They own several restaurants, including Girl & the Goat and Duck Duck Goat. Check out either of these options for a deliciously satisfying meal that won’t disappoint. If you’re looking for a more immersive dining experience, try Carnivale, a Latin-fusion restaurant that’s colorfully decorated and frequently has live entertainment. Or check out Proxi, which boasts a four-course Chef’s menu that will take you all across the culinary world. 

If you’re looking for a nightcap, head over to Recess, an indoor/outdoor bar with a laid-back vibe; or spend some time at Emporium, an arcade bar that truly has game options for everyone. Prefer to round out the night with a delicious treat? Swing by Black Dog Gelato for a homemade, inventive frozen dessert. 

sunday.

We’re heading to the north side for Sunday Funday! Hop on the red line of the L, or if you’re feeling a little adventurous, rent a Divvy bike and ride up the Lakefront Trail. The views never disappoint! The north side of the city has more of a homey vibe than downtown – think picturesque streets lined with gorgeous low-rises, delicious restaurants that feature truly any type of cuisine you could want, and independently owned boutiques and shops. 

Stop for breakfast at one of the north side’s diner-like spots: Batter & Berries (known for their french toast flight) or Ann Sather (incredible cinnamon rolls). If you want a slightly more luxe brunch spot, check out Maison Marcel, a super Instagrammable French-American cafe. 

After breakfast, head over to the Lincoln Park Zoo. Admission is free, and they offer several self-guided tours if you want to learn along the way. Once you’ve seen all the furry friends the zoo has to offer, it’s time for an afternoon pick-me-up! Chicago is 420-friendly, so if you’re wanting to partake, check out Wake-n-Bakery. They offer THC-infused baked goods and beverages, like coffees, teas, and lemonades. If you’re new to the world of THC, don’t worry! The staff is super helpful and friendly and will help you find an infusion that’s right for you; or, you can always order any of their drink options without an infusion. 

Enjoy your drink as you stroll through Lincoln Park (you’ll be right by Belmont Harbor, which houses lots of impressive yachts and sailing boats); or, head over to Wrigley Field. Even if you’re like me and couldn’t care less about baseball, it’s a really beautiful and impressive historical structure to see. 

For dinner, try out Athenian Room, a Greek restaurant home to Tina Fey’s favorite Chicago meal; Sapori Trattoria, an intimate Italian spot; or, one of my absolute favorites, Cafe Ba-Ba-Reeba. Make sure to order a pitcher of sangria to share (or not to share, I’m not here to judge), and you truly can’t go wrong with any of the tapas here – the spicy potatoes, ham croquetas, and baked goat cheese are just a few of my recommendations. 

To round out the night, go see a show at one of Chicago’s comedy clubs. You’ll be close by to Zanies, The Second City, and Laugh Factory, all of which offer shows 7 nights a week; just make sure to check their websites ahead of time to see exactly what they’re hosting and if you need to purchase tickets or reserve a seat. Their shows never disappoint, and you’ll end your trip with a solid dose of serotonin-inducing laughs! 

If you’re planning a trip to Chicago or thinking about planning one, feel free to reach out to me! There is so much to do in this awesome city, and this list just begins to scratch the surface of everything you can do here. Happy travels!