The Windy City Tips:

Mmmm it’s windy. Really though. The winters can be insanely brutal, pack appropriately.
Chicago is pretty huge, so be sure to plan ahead so you’re not driving/Lyfting all over the place

Adventures & Ales Top Recommendations:

Phase Three Brewing: A fantastic brewery in an industrial park in Lake Zurich. They have incredible beers of all styles, an outside space and frequent food trucks.
Maplewood Brewery and Distillery: Absolutely delightful spot with amazing beers and a fun lounge atmosphere.
Whisk: A fantastic brunch option that is BYOB and cash-only. Get the biscuits and gravy—ya welcome.
More Brewing: In the ‘burbs of Chicago, this brewery is cranking out fantastic beers of every style.
Mikerphone Brewing: A fun music themed brewery with incredible beers. Close to O’Hare Airport as well!
Forbidden Root Brewery: They have their own herbs and fruits they grow and infuse into their beers—get the Strawberry Basil Hefeweizen. Also cheese plates.

Begyle Brewing: Great beers and a fun atmosphere!
Dovetail Brewery: A Lager-focused brewery that is right around the corner from Begyle with solid beers. They also have a small food menu and an outdoor bar in the summer months.
Half Acre Beer: A large taproom both inside and out with a plethora of beer options. They also have a small food menu. Keeping Together, a Mixed Culture project from Averie Swanson is housed here as well with draft and bottle options.
Local Option: A super fun beer bar with a full food menu and frequent events. Their tap list is killer!
Beermiscuous: A great beer bar and bottle shop with 16 taps and to-go cans and bottles. They offer single cans which is fantastic to get a variety of things.
Parlor Pizza: Delicious pizzas and a great tap list.

The Classic Tourist Spots Actually Worth Visiting:

The Bean: Obviously you can’t go to Chicago without a stop at The Bean! Expect hoards of tourists.
Explore the Lakefront Trail! This 18 mile path runs along Lake Michigan through various parks and attractions.
The Signature Room at the 96th: The views are stunning but the drinks are pricey, it’s worth checking out!
Wander Logan Square: Get a bagel sandwich from Brobagel, pop into some shops!
Take an architecture tour!
Pequod’s Pizza: Fantastic deep dish (insert drool here)
Ohio Street Beach: A popular sandy beach on the lake with skyline views downtown. Close to navy Pier.
Montrose Beach: A popular area for walking, biking, dogs, volleyball, and a beach on Lake Michigan.

Other ideas:

Revolution Brewing: One of the most popular breweries in the city. They have a wide array of beers but their Stouts are particularly great.
Old Irving Brewing: Great beers and a full food menu. More of a restaurant-style set-up than brewery.
Pilot Project: A brewery incubator housing small, new breweries as they get their start. They have a great patio and a beautiful indoor space. Located in the Logan Square neighborhood.
Marz Brewing: A cool spot not too far from Midway Airport with solid beers.
Hubbard’s Cave/Une Année: This unique space started with Une Année producing Belgian beers and then expanded with Hubbard’s Cave specializing in Stouts and IPAs. They have BBQ onsite and a large outdoor space.
Goose Island: Not my favorite because Anheuser Busch owns them, but they’ve got quite a few unique beers only at their Chicago brewery.
Stan’s Donuts: I am a sucker for a good doughnut and Stan’s does not disappoint!
Taste of New York Bagels and Deli: A pretty authentic NYC bagel spot near Wrigleyville.
Corridor Brewery & Provisions: A restaurant-style brewery with average beers. The tap list is quite small. Located near Wrigleyville in a popular neighborhood.
District Brew Yards: Around the Bend Beer Co., Bold Dog Beer Co., and Casa Humilde Cerveceria Artesanal all under one roof with food and games