Madison & Charlie’s guide to:
Chicago, Illinois
Why chicago?
Chicago is our home! Even though we have moved 8 times in 3 years, we are both from the Chicago suburbs and finally live back in the city again. We met in Chicago in 2018, and have since been to many bars, restaurants, events, and really just about anything under the sun. We hope you enjoy our recommendations!
Disclaimer!
These are our favorite places, but may not be yours. Our recommendations are also catered towards the North Side, where we live. If you want a detailed “Best of Chicago” list, we recommend checking out Lonely Planet or Time Out.
Where in Chicago…
You may be wondering, where in Chicago can I find _____? To start, it’s helpful to know a little about the Chicago neighborhoods
North side
The Northside includes neighborhoods like Lincoln Park, Old Town, Lakeview, Andersonville, and Uptown.
Where we live!
west side
West of the city includes neighborhoods such as West Loop, Wicker Park, Bucktown, Ukrainian Village, Logan Square, and Humboldt Park.
south side
The Southside includes neighborhoods like South Loop, Bronzeville, Hyde Park, and Chinatown.
the loop
The Loop is what you imagine! Named for the loop of the elevated subway (the “L”). The Loop includes neighborhoods like River North and Streeterville.
Places to eat/drink
Downtown/The Loop
Beatnik on the River
Three Dots and a Dash
Flight Club
Tortoise Supper Club
Chicago Athletic Association/Cindy’s Rooftop
Bavette's Bar & Boeuf
Cardozo’s Pub
North side
Three Arts Cafe
Tweet/Big Chicks
Wilde Bar
Pingpong
The Green Mill
Korzo Cafe
Gather
The Butcher’s Tap
Elixir Lounge
The Chicago Diner
Wood
Lark (we go there for trivia!)
West Side
Parlor Pizza
Moneygun + St. Lou’s Assembly (we got engaged there!)
Punch Bowl Social
Map Room
The Violet Hour
South Side
Pleasant House Pub
Punch House/Thalia Hall
Simone's
Skylark
Queen Mary
Rainbo Club
Phyllis’ Musical Inn
Scofflaw
Mac's Wood Grilled
things to do
Go to a sporting event
We’ve kinda got it all here (though don’t expect a win): Bears, Cubs, Sox, Blackhawks, Sky, Red Stars, Fire
Attend a concert
We are lucky in Chicago to always have major artists come through!
Go out dancing
We live in Boystown, so we are a bit biased towards Sidetrack and Roscoe’s, but Beauty Bar is our other fav. We also love Kingston Mines for a late-night-live-music adventure.
Join a rec league
We’ve done soccer and cornhole, but there is something for everyone. Chicago Sport & Social is the most famous league, but there are more specific ones for certain sports!
See a show
Broadway in Chicago is famous, and major shows are always coming through. Pro tip: check out the Broadway in Chicago Facebook page on the 25th for $25 tickets!
Chicago is also famous for its comedy scene! Check out the Second City, IO Theater, and Annoyance Theater, to name a few.
Chicago is originated the concept of dinner + magic, and The Chicago Magic Lounge is a great choice. The Trickery is also a fun option for magic.
Take a class
I’m currently taking Irish Dance class at the Old Town School of Folk Music, and I’ve also taken a cake decorating class at Bon Vivant Cakes, made charm necklaces at Beadnicks, and cooked at Get in the Kitchen!
Seasonal events in Chicago
Chicago is a festival city! We also get ALL of the seasons. Whether you’re bundling up or sweating it out, Chicago has something you’ll enjoy.
Summer
There’s pretty much a festival (or multiple) each day in the summer, so take your pick!
Pride Fest
Market Days
Taste of Chicago
Lollapalooza
Renegade Craft Fair
Lincoln Park Greek Fest
Do Division Street Fest
Andersonville Midsommarfest
Full Moon Jam
Belmont-Sheffield Music Fest
Chicago Humanities Festival
Open House Chicago
Sueños Music Festival
Winter/Spring/Fall
Christkindlmarket (hoping they have it back in Wrigley next year)
Renegade Craft Fair (again!)
Chicago Artisan Market in Ravenswood
St. Patrick’s Day
This is a crazy holiday in Chicago - it’s worth seeing the river dyed green once and that’s it
Lincoln Square Apple Fest
How to get outside
A lot of people don’t realize that Chicago has beaches! Sure… they may be lake beaches, but when you can’t see the other end, it’s kinda like an ocean, right?
Go on a boat ride on the lake
Many of these boats leave from Navy Pier, which can also be fun to check out (but it’s a tourist trap so don’t stay long).
Hang out at the beach
We personally love Foster Beach and Montrose Beach. If you have a dog, check out Montrose Dog Beach (but maybe not at peak times)!
Rent a boat to take down the Chicago River
Renting a boat through the Chicago Electric Boat Company is surprisingly affordable and so much fun - make sure you have a sober captain though.
Another not to miss is the Chicago Architecture Tour. It may seem cliche, but it is the best way to learn about the city.
Rent a Divvy bike down the Lakefront Trail
Pro tip: get the ones with the electric pedals - you’ll thank me later.
Walk around the neighborhoods!
Chicago has some of the most unique and lovely architecture, and simply walking through neighborhoods like Lincoln Park can be a fun pastime.
