Chicago Newcomer's Guide (By a Local!)

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Are you new to Chicago? If so, you’re going to want to bookmark this page.

This Newcomer’s Chicago Cheat Sheet includes a ton of resources to help you adjust to your new life in the Windy City. It includes links to platforms and social groups where you can meet new friends (by the way, we have a Travel Lemming Chicago meetup group!). You’ll find links to recreation resources if you want to join a sports league or pick up an arts class. Plus, there’s so much more.

As a Chicago transplant myself, I wish I’d had a Chicago cheat sheet like this one. It’s my hope that this will help kickstart your new chapter in Chicago so you grow to love the city as much as I do.

And if you don’t see what you’re looking for, feel free to ask me in our Chicago forum!

I’ve made this guide easy to follow, so you can get right to the point, and find whatever you’re looking for.

The Chicago Cheat Sheet (found below) is the meat and potatoes of this article. This is where you’ll find links to tons of Chicago resources. I’ve included everything from places to make friends to a quick neighborhood breakdown and even what the local hospitals are.

The FAQ section has answers to commonly asked questions. I cover popular topics like safety, weather, and real estate.

The Ask Us a Question tab leads you to our Chicago Forum, which is the perfect place to get personalized advice.

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Your Chicago Newcomer’s Cheat Sheet

👫 Making Friends

Social Groups:
Travel Lemming Chicago Meetup – Our own monthly meetup!
Chicago Girls Who Walk
Chicago Gents Who Stroll
Sunday Morning Club
The Friendwork Collective
Let’s Be Friends
Pals Party Chicago

Sports:
Chicago Sport & Social Club
Players Sport & Social Group
Chicago Run Collective
Shut Up and Run Club
All Bodies on Bikes
Chicago Jump Club
Women’s Sports Chicago
Basketball Watch Club

Arts, Culture, & Games
Chicago Book & Social Club
Chicago Book Club
Chicago Craft Club
Chess Club Chicago
Chess Night
Pinball Chicago
Cheeky Makers Club

Food & Drinks
Girl Dinner Social
Chicago Bake Club
Chicago Dinner Club

Volunteering & Community Work
Chicago Cares
Greater Chicago Food Depository
PAWS Chicago
Trash People of Logan Square

Platforms for Finding Events
Meetup.com
Pie Social
Meet IRL

Be consistent – Go to the same places often and talk to people. Be consistent.

Don’t lose hope – It takes time to build your community. Don’t be discouraged.

Try a lot of things – Try a lot of activities and social events to make friends. You never know where you’ll meet your people.

Put yourself out there – Making the first move is always the scariest.

Talk to strangers – Chicagoans are friendly and approachable. Talk to strangers!

Meet friends of friends – This is one of the easiest ways to make new connections.

🗣️ Local Culture

“The Loop” – This refers to the heart of downtown Chicago. All of the train lines meet in this part of the city, forming a loop. Hence, the name. If you hear someone referring to “the Loop” they’re talking about downtown Chicago.

“The L” – This refers to the train. Saying “the L” is an abbreviation of “elevated” because Chicago’s trains are mostly elevated instead of underground. This being said, many locals just call it a train, too.

CTA – This stands for Chicago Transit Authority.

“Yeah, no” – This means yes. You’ll hear Midwesterners say this a lot.

For more Chicago history and trivia, see my list of fun facts about Chicago.

People – Generally down-to-earth, friendly, open, and approachable.

Clothing Style – Mix of everything. Very casual to trendy and stylish.

Pace of Life – Somewhat fast-paced but also relaxed, especially in summer.

Politics – Chicago heavily leans Democratic.

Languages – You’ll hear many different languages across the city.

Geography – Chicago is totally flat and sits right on Lake Michigan.

Weather – Expect all 4 seasons, with winter & summer being most extreme.

Driving – Rushed, impatient, fast-paced.

Transportation – Chicago is driveable, walkable, bikeable, and has good public transport.

Nightlife – Totally depends on the neighborhood if nightlife is prominent.

River North – A rowdier, more club-like nightlife scene.
West Loop – Swankier, more upscale bars.
Wrigleyville – Lots of sports bars.
Wicker Park – A mix of dive bars and speakeasies.
Logan Square – Cool, eclectic bars and dance-y bars.
West Town – Dive bars and dance-y bars.

City Center:
The Loop – The heart of downtown Chicago.
River North – Just north of the Loop. Restaurants and nightlife.
Magnificent Mile – Chicago’s famed shopping street.
Streeterville – High-rise apartments, shops, and hotels.

West Side:
West Loop – Trendy foodie neighborhood & shopping area.
West Town – Relaxed, eclectic, melting pot.
Wicker Park – Artsy, trendy, and buzzing vibe.
Logan Square – Cool, eclectic neighborhood with a creative vibe.

North Side:
Gold Coast – Wealthy neighborhood with historic homes & luxury shopping.
Old Town – Laid-back area with shops and comedy clubs.
Lincoln Park – Very green and residential neighborhood.
Lake View – Diverse shops and restaurants, close to the lake.
Wrigleyville – Sporty vibe. Home to Wrigley Field.

South Side:
Hyde Park – Historic and home to the University of Chicago.
South Loop – Residential high-rise area, close to museums.
Pilsen – Mexican/Latino neighborhood.
Chinatown – Chinese and largely Asian neighborhood.

This is by no means an exhaustive list, but it should help you get a general idea of popular areas. See my guide to Chicago’s neighborhoods for a deeper dive.

🍽️ Food & Drink

Deep-Dish Pizza – This is the food that most people identify with Chicago. Deep-dish pizza is kind of like a pie, with layers of cheese, sauce, and toppings, and a thick crust. Deep-dish is baked.

Tavern-Style Pizza – Chicago’s lesser-known pizza style known for its thin, cracker-like crust and toppings that go all the way to the edges.

Malört – A Chicago liqueur known for its bitter, herbal, and intense taste. It’s traditionally made from wormwood and is known for its distinctive bad taste. Jeppson’s Malört is the only “true” Malört.

Old Style – A popular beer in Chicago.

Chicago Handshake – A rite of passage for Chicago newbies. This consists of taking a shot of Jeppson’s Malört then chasing it down with an Old Style lager.

Chicago-Style Hot Dog – An all-beef hot dog in a poppy seed bun topped with yellow mustard, tomato, white onion, sweet pickle relish, pickled sport peppers, a spear of dill pickle, and some celery salt.

Italian Beef Sandwich – Chicago’s “official” sandwich. A French roll filled with thinly sliced beef and topped with giardiniera and Italian sweet peppers, with beef au jus for dipping.

See my article if you want to know about other Chicago foods!

Girl & The Goat – One of Chicago’s top restaurants. Perfect for special occasions.
Au Cheval – Ranked for “best burger in America.”
Kasama – The first Michelin-starred Filipino restaurant in the world.
Lula Cafe – A local favorite with delicious brunch & dinner.
Qing Xiang Yuan Dumplings – The best dumplings in Chicago.
Doma – Hidden gem with amazing breakfast and baked goods.
Pequod’s Pizza – Local favorite for deep-dish pizza.

See my full list of Chicago restaurants for more ideas.

Sugar Moon – Hidden gem in Logan Square. Amazing desserts.
Mindy’s Bakery – Wicker Park bakery. Everything is amazing.
Doma – Hidden gem with delicious brown butter cookies.
Bang Bang Pie & Biscuits – The best pie in Chicago.
Annette’s Italian Ice – Local favorite with delicious Italian ice.

See my favorite dessert spots in Chicago article if you’re looking for more!

These are some Chicago bars worth checking out:

Cindy’s Rooftop – Upscale rooftop bar that overlooks Millennium Park.
The Violet Hour – Wicker Park speakeasy with craft cocktails.
Fadó Irish Pub – Irish sports bar in River North.
The Whistler – A fun, dance-y bar in Logan Square.
Lazy Bird – Swanky cocktail bar in West Loop.
Roscoe’s Tavern – Lively LGBTQ+ bar in Lakeview.
Emporium Arcade Bar – Arcade bar with multiple locations.

😊 Recreation

Family Play Groups:
Chicago Family Picnic
Playgroup North Shore

Playgrounds:
Oz Park
Maggie Daley Park
Bartelme (Mary) Park
Bauler Park Playground
Hamlin Park Playground
Goudy (William) Square Park
Lincoln Playground-Cummings
Lake Shore Playground
Jefferson Park Playground
Chicago Park 540 Playground
Bosley (William) Park
Bixler Park Playground

Scouting:
Chicago Cub Scouts
Girl Scouts of Greater Chicago

Youth Sports:
Chicago Rec Sports
Lil’ Kickers – Soccer for Kids
i9 Chicago Youth Sports Leagues
Chicago Fire Youth Soccer Club
Fit City Kids

⚕️ Health & Safety

Northwestern Medicine
Advocate Health Care
RUSH Primary Care

Northwestern Memorial Hospital
RUSH University Medical Center

I recommend downloading the following apps:

ParkChicago – This is what you’ll use to pay for street parking around most of Chicago.
Ventra – This is where you can add money to your account to ride public transportation.
Divvy Bikes – This is the bike rental app you’ll use in Chicago.
The Nudge – Sign up for texts to receive fun recommendations for things to do and upcoming events.

Chicago Public Library
Chicago Public Schools
Chicago Police Department
Chicago Transit Authority

❄️ Surviving Winter

Clothing:
Coat – You need a coat that’s knee-length or longer. Trust me.
Gloves – Invest in good gloves with screen compatibility.
Scarf – Having one is a good idea.
Hat – An absolute necessity.
Boots – Invest in warm, waterproof boots with good grip.
Balaclava – You don’t need this, but it’s nice to have if it’s truly freezing.

Other Things:
Snow Brush & Ice Scraper – You need this.
Heated Blanket – A game changer.
Space Heater – I think everyone in Chicago should have one.
Shoe/Boot Tray – Helpful for keeping your floors clean from snow and salt.
Vitamin D Supplements – Seasonal Depression is real here. Vitamin D can help.

Layer up – Wear lots of layers and invest in good gear.

Get out of the house – Seasonal depression is real. Be intentional about making plans and seeing people.

Go to museums – This is a great time of year to enjoy Chicago’s museums with fewer crowds.

Try new restaurants – Similarly, this is a great time to enjoy indoor dining!

Go ice skating – Chicago has 2 great outdoor rinks in Millennium Park.

Sign up for a class – This is the perfect time of year to sign up for classes like pottery, music, learning a language, etc.

Walk the Lakefront Trail – With the right layers and gear, a walk can be enjoyable.

Soak up the holidays – Lean into the holiday festivities. It’ll help you get through December.

Plan a vacation – January and February are tough. Plan a vacation to someplace warm (and enjoy cheaper prices, too!).

🐶 Pets in Chicago

Adoption:
PAWS Chicago
One Tail at a Time
Anti-Cruelty

Dog Parks:
Montrose Dog Park
Jackson Bark Park
The West Loop 569 Dog Friendly Area
Wiggly Field Dog Park
Puptown Dog Park

Dog Beaches:
Montrose Dog Beach
Belmont Harbor Dog Beach

Dog-Friendly Spots:
Ludlow Charlingtons Coffee Shop
Bandit
Cody’s Public House
Ranalli’s
Clark Street Alehouse
Central Park Bar
Park & Field
Recess

Chicago is a generally safe place to live and visit. Despite what the media and news portray, Chicago’s crime is comparable to other major metropolitan areas. And, most violent crimes that occur happen in specific areas outside of the city.

This being said, property crime is the most common type of crime. Next, I’d say to be mindful of homeless individuals. Weather hazards also pose a risk during the winter. For a full breakdown of safety, see my guide: Is Chicago Safe?

The average salary in Chicago is 74,544 [Source]. The average cost of living is 14% higher than the national average [Source]. Rent can vary a lot by neighborhood, so consider this when finding a place to live. But generally, a one bedroom apartment can fall anywhere from about $1200 to $2000, depending.

Chicago is a great place to live for people of many interests and backgrounds. But if you’re looking for a specific “vibe,” this is what I’d say:

Chicago is the perfect place to live if you’re looking for a big city vibe and all the amenities, but prefer a more laid-back, down-to-earth vibe. Similarly, if walkability and accessible recreation are important to you, Chicago offers that in spades.

It’s truly a city for all interests and backgrounds. People who enjoy arts and culture will enjoy the city as much as someone who loves sports. At the same time, Chicago is a great shopping and food destination, while it also has activities for those who enjoy the outdoors. It’s family friendly as well as a great place for young professionals and retirees.

Technically, you don’t need a car to live in Chicago. However, having one really does come in handy for getting around the city. It just has its pros and cons.

First, don’t expect to get your own parking spot (especially covered, garage parking) unless you’re willing to pay for it. In most cases, residential parking is street parking, and it’s done by zone.

The pros of having a car in the city is that it’s far more convenient to run errands and explore neighborhoods farther from you. It’s also easier to take day trips from Chicago. Driving itself is pretty manageable here. The downsides are that parking can be annoying or difficult, gas is expensive, and your car might require more maintenance due to the snowy conditions and salt in the winter.

The pros of not having a car is that you never have to worry about parking and you’ll likely save some money in the long run. However, expect to get extremely familiar with public transportation.

Finding the right neighborhood is arguably the most important decision you’ll make when you live in Chicago.

I recommend defining what “vibe” you want from your soon-to-be neighborhood. Do you want something quiet and residential? Close to the lakefront? Full of bars and restaurants? Maybe you’re looking for a modern high-rise. Maybe you prefer an older brownstone.

After this, make a list of other important factors such as budget, access to public transportation, and school system.

When all is said and done, just because you choose one neighborhood, it doesn’t mean you’re tied to it forever. You likely won’t find your “perfect” neighborhood until after you’ve lived here for at least a year.

The real estate market in Chicago moves fast, but it’s not as cutthroat as, say, New York City’s. That being said, Chicago is a big city with a high demand for apartments. You don’t have the luxury of seeing a place, thinking about it, then moving forward with your application. Know what you’re looking for, decide what your non-negotiables are, and be prepared to apply or sign on-site. Decisiveness is key.

For my current apartment, I messaged the broker as soon as I saw the listing and made an appointment for the next day. I showed up early to the showing in order to be the first person in line. A handful of people were touring at the same time as me. In order to get ahead, I sent in my application about 10 minutes into the tour. The principle of “first come, first serve” definitely applies to Chicago’s real estate market. That, and having all your paperwork and information ready to go.

Chicago has a good job market with the top industries being food & manufacturing, finance, and innovation & technology [Source]. Healthcare, transportation, and hospitality are also big players. According to World Business Chicago, the Windy City has the 3rd largest US Metro economy and 31 Fortune 500 companies.

Aside from corporate jobs and larger businesses, Chicago is rich with small, independent businesses.

Chicago has the third largest school district in the country, and is generally above average. This being said, the quality of education really varies by neighborhood.

The areas of Chicago with higher rated schools also reflect Chicago’s map of redlined and wealthy neighborhoods, which is another complicated issue, but one that has real implications on the city’s school system. Schools on the city’s north side largely perform better than schools in the west and south sides.

Chicago is home to some of the top high schools in the nation, including Payton College Preparatory High School. Northside College Preparatory High School and Whitney M. Young Magnet High School also rank highly. [Source, Source]

Chicago’s schools received a B rating from Niche.com.

The main universities in Chicago are:

The University of Chicago
DePaul University
Loyola University
Northwestern University (located in Evanston)
University of Illinois Chicago

Chicago is a diverse city. As of July 2024, the racial makeup is 39% White, 28.4% Black, 29.6% Hispanic or Latino, 7.1% Asian, .9% Native American, and .1% Native Hawaiian or Pacific Islander. Additionally, 32.2% are White alone, not Hispanic or Latino, and 12% are two or more races. [Source]

Now, anecdotally, I’ll say that Chicago does feel racially diverse. However, there are definite racial differences by neighborhood and area. Along the same lines, Chicago is home to rich cultural communities such as Chinatown, Pilsen, Ukrainian Village, Little Italy, Andersonville, Bronzeville, and others.

For members of the LGBTQ+ community, Chicago is quite liberal and diverse. Boystown and Andersonville are especially LGBTQ+ friendly.

See my guide to Chicago’s neighborhoods to learn more.

Chicago experiences all four seasons, with winter and summer bringing the most extremes in terms of temperatures. It’s true that Chicago’s winters are freezing and often snowy. However, in recent years, winters have been milder with less snowfall and slightly milder temperatures.

Springtime in Chicago is unpredictable, with temperature fluctuations and many rainy days. Temperatures consistently become warm in June. Summers are hot, but extremely fun. The city comes alive and Lake Michigan beaches provide a refreshing reprieve from the sun. Fall is mild and foliage peaks around mid-to-late October.

See my guide to the best time to visit Chicago.

Have a question? Join our brand new forum and post a question there. Our Chicago local, Lea Rose, will get back to you.

Chicago Travel Forum

Looking for more? See our guides to Chicago!