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A Local’s Travel Guide to Chicago: Where Urban Pulse Collides With History

Welcome to our Chicago travel guide. Here you’ll find key details about the city, including best times to visit, how to get around, and key things to know about the culture.

Aerial View of Chicago Skyline in Summer
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Key Details

Province/State: Illinois

Country: United States

Population: 2,693,976

Time Zone: Central

Languages Spoken: English

Currency Used: USD

About Chicago

Whenever I come home to Chicago from time away, I listen to the song “Chicago” by I Fight Dragons. Although many artists have made songs dedicated to my heart city, this one always hits the strongest.

The jewel beside Lake Michigan, Chicago, is the third largest city in the United States. Also known as the Windy City (because of high falutin egos, not actual wind), it is my favorite city in the world. When you visit Chicago, you’ll understand how I fell in love with it and had to move here.

Chicago famously burned almost to the ground during the Great Chicago Fire in 1871. That is how it got the other nickname of The Second City. It is a city reborn. Chicago is known for its incredible art scene, shopping along the famed Magnificent Mile on Michigan Avenue, and (my favorite) deep-dish pizza. Yet this incredible city is so much more than all that.

“Oh Chicago knows how small we are/How bright she shines in the dark/Oh and though I go, she’s in my heart/Chicago holds me when I fall apart”

-“Chicago” by I Fight Dragons

Best Time to Visit

To me, Chicago is a destination all year long. Seeing the rippling Chicago River in springtime, Lincoln Park Zoo in winter, Millennium Park in autumnal splendor, or downtown Chicago in the bustling summer is just too perfect. But if you aren’t a wintertime wanderer like me, you may want to consider the range of Chicago’s seasons.

June to August: Peak tourist season in Chicago is the summer. The weather is hottest (Midwestern humidity is no joke), and the city is the most crowded. This is our festival season, so there is plenty to do, yet hotels will also be at their most expensive. Hit up North Avenue Beach or Oak Street Beach if you need a dip in the lake.

March to May or September to October: Chicago’s shoulder season, these months offer far cheaper accommodation and activities than the summer. The weather is relatively mild, especially in May or September, with warm temps and lovely spring or fall colors.

November to February: Despite the unpredictable winter months in the city, these are my favorite months for visiting Chicago. Particularly if you’ll be spending time in the city center, it’s much easier to explore Chicago when the weather gets colder. Far fewer tourists, cheaper hotel rates, and the romantic snow? Sold. Just don’t underestimate the bitter wind.

About the Area

I always say you don’t know Chicago until you know its neighborhoods. The city limits have 77 distinct neighborhood areas that give the city its gravitas. You will probably spend much time downtown or in the Loop area. Still, you can’t possibly get to know them all in a single visit, though there are a handful I recommend you consider before your next trip.

  • Andersonville: One of the city’s largest LGBTQIA+ communities, Andersonville is an adorable neighborhood on the North Side. You’ll find lots of brunchy spots, unique boutiques, and ways to spend an afternoon.
    • Swedish American Museum
    • Chicago Magic Lounge
    • The Neo-Futurists
  • Gold Coast: A historic neighborhood, the Gold Coast is lined with incredible homes that once belonged to some of the city’s most rich and powerful. It is a beautiful neighborhood to walk around or dine in one of its delicious restaurants.
    • Museum of Contemporary Art Chicago
    • Navy Pier
    • Gibsons Bar & Steakhouse
  • Grant Park: While it is called Millennium Park, it is actually part of the much larger Grant Park. The neighborhood that shares its name is where many of the city’s big attractions reside, including the massive Museum Campus.
    • The Art Institute of Chicago (one of the largest art museums in the world)
    • Cloud Gate
    • Shedd Aquarium
    • The Field Museum (the natural history museum)
  • Hyde Park: Famously known as being home to former President Barack Obama, Hyde Park houses one of the only buildings left from the World’s Columbian Exposition. This neighborhood on the city’s South Side is an incredible glimpse into Chicago’s past.
    • Museum of Science and Industry
    • Promontory Point (perfect for photographing the Chicago skyline)
    • DuSable Black History Museum
    • Frederick C. Robie House (a Frank Lloyd Wright home and historic landmark)
  • Logan Square: Home to a range of Chicago style homes, Logan Square is one of the more trendy areas in the city. Here is where you can do some excellent sightseeing in a more local way. Enjoy some bar hopping or indulge in a food tour.
    • The 606 (a pedestrian trail)
    • The Logan Theatre
    • Emporium Arcade Bar
  • River North: A neighbor to the Gold Coast, the River North area is another luxe part near downtown. You’ll find lots of restaurants and bars here, as well as a handful of attractions like Willis Tower (Sears Tower, as many of us still stubbornly call it).
    • Merchandise Mart
    • House of Blues Chicago
    • Richard H. Driehaus Museum

How to Get There

Getting from the O’Hare International Airport to downtown is pretty easy. There are several ways to go about it.

The L – Blue Line: The most convenient, cheapest, and often fastest way to get downtown is by riding the Blue Line. It picks up right at O’Hare! This train runs 24/7, so there is no need to worry about arriving too early or too late to grab a train. Depending on when the train arrives, it takes about 45 minutes to get downtown from the airport.

Taxi: Personally, I usually take a taxi home from the airport. It’s usually cheaper than rideshare, there is always a line of them at the stand, and it’s just more convenient for me. If you’re staying in an area of the city off of the Red Line rather than the Blue Line like I do, it’s a better option.

Rideshare: Rideshare has never been very convenient at O’Hare. When the airport decided to relegate all of the rideshare pickups to outside Terminal 2, it made them even less convenient. You can still call a rideshare, but you will need to go to the Terminal 2 pickup area to do so.

Shuttle Pickups: Some hotels offer free or paid shuttle pickups from the airport. These will be cheaper options than rideshare or taxi, though you may be waiting a little while for other passengers before you depart.

How to Get Around

We don’t have patience for lack of etiquette on Chicago public transportation. We use these buses and trains day in and day out. Use common sense when riding and don’t do things like block doors or exits or crowd the doors as the train approaches. Let passengers off before you push your way on. I promise your time here will be a lot more pleasant if you use common courtesy on public transit.
The L: Our “elevated train” or “the L” is one of the best ways to get around the city. Operated by the Chicago Transit Authority, you’ll frequently hear people just refer to it as the CTA. There are eight train lines which are all named by color. While not perfect, the L is usually more reliable than the buses.

Buses: I’ll be honest, I usually avoid the buses. They’re notoriously unreliable in the neighborhoods outside of downtown. As a visitor, you’ll probably be downtown a lot of the time, so this may not affect you as much. Still, you can often get places more quickly on foot than waiting for a ghost bus.

The Metra: Not to be confused with the L, the Metra trains are more direct to further away points. They’re excellent for getting from downtown to some of the suburbs, for example. Please note that this will not take you to the airport.

Chicago Water Taxi: These fun little boats will take you to a few different locations down the Chicago River. It’s a fun, unique way to get from point A to point B.

Taxis: We still have a ton of taxis in addition to rideshares in Chicago. Personally, I prefer taxis for drives like from the airport back home. Mostly because they are priced competitively with rideshare companies and will often show up more quickly.

Rideshare: Rideshares since 2020 have been hit or miss, especially downtown. You may end up getting hit with surge pricing more often than not. It’s best to have a taxi app like Curb to compare prices with.

Pedicabs: Just don’t do it.

Here’s a summary of the key methods of transportation around Chicago along with key stops and services:

Transit Option Description Key Stops/Services
CTA Buses Extensive network covering all of downtown Chicago with frequent service. Michigan Avenue, State Street, Museum Campus
CTA Trains (“The ‘L’”) Rapid transit system with multiple lines serving downtown. Loop ‘L’ (elevated tracks), Red and Blue Lines (subway)
Metra Trains Commuter rail with stations in downtown connecting to suburbs. Millennium Station, Ogilvie Transportation Center, Union Station
Divvy Bikes Bike-sharing service with numerous docking stations throughout downtown. Navy Pier, Millennium Park, Willis Tower
Taxis/Ride Share Readily available throughout downtown for direct, convenient travel. Hotels, tourist attractions, business districts
Water Taxis Seasonal service providing scenic routes along the Chicago River. Michigan Avenue, Chinatown, Willis Tower

Cultural Heritage

Chicago doesn’t get enough credit for the vast cultural diversity it houses. The city has been an epicenter for music and artistic development as well as the merging of countless heritages. It is considered one of the most culturally diverse cities in the country. Many groups of immigrants came to the city in the 19th century, including the Irish, German, Polish, Italian, and Bohemian (now Czech).

The conglomeration of cultures led to a swath of food traditions in Chicago as well. From the beloved Chicago hot dogs to the Italian beef sandwich, Chicago does comfort food so well. You just can’t beat a good Chicago dog on a bad day, ya know? You can thank our Germanic roots for the wurst-based menus here.

You’ll see the uniqueness of Chicago’s heritage anywhere you go in the city. From our art-filled Chicago Riverwalk to the Chicago architecture. Our city is just built differently. That’s one of the reasons why it’s such a special place to be.

Customs & Etiquette

First things first, we are serious about our Chicago-style Dogs. Ketchup? We don’t do that — well, I do if it’s just a plain dog. That’s because an actual Chicago Dog is topped with a ton of things already: white onions, pickle relish, yellow mustard, a dill pickle, tomato, pickled sport peppers, and celery salt. You can put ketchup on a hot dog here, but if you’re in public, you might get side-eyed by a local. Don’t worry about it, our bark is worse than our bite.

We have a reputation for being gruff. What you need to remember, though, is that Chicago is part of the Midwest. So even if we do walk faster because we’re city dwellers, we are genuinely kind. If you’re wandering around Lincoln Park and need directions, we’ll help you out. We are genuinely happy to share our city with visitors. I, for one, want you to have the best visit possible.

That said, please don’t come and talk about how “dangerous” our city is. That’s like walking into someone’s home and talking about how much you hate the wallpaper. No place is perfect, and the rumors of Chicago are greatly exaggerated. It really sucks to be in public and hear someone from out of town railing about the place they’re visiting — a frequent occurrence when I ride the train in the touristy summer. Chicagoans are fierce defenders of their beloved city. We’d prefer if you kept your comments to yourself, we aren’t interested in hearing it.

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