Welcome to my favorite city in the world, the Windy City, aka Chicago. A place where towering skyscrapers meet the tranquil shores of Lake Michigan, with vibrant neighborhoods full of energy and diverse cultures. Chicago, a city famed for its architectural marvels, deep-dish pizza, creation of house music, and illustrious jazz history, offers a mosaic of experiences that cater to every type of traveler.
As a relocated local since 2018, I've had the unique pleasure of experiencing Chicago beyond its glittering tourist attractions. I created this guide based on my time exploring Chicago to help you make the most of your time here, from must-see sights and hidden gems to the best local experiences.
Planning your Visit:
Chicago History:
Chicago, founded in 1833, quickly grew from a small settlement to a major metropolis due to its strategic location. The Great Chicago Fire of 1871 devastated the city but also paved the way for innovative urban planning and architecture, leading to its nickname "The Second City" due to its phoenix-like rebirth. Throughout the 20th century, Chicago became a cultural and economic hub, famous for its contributions to music, particularly jazz and blues, its significant architectural movements, and as a crucible for modern industry and labor movements. You can learn more about the history of Chicago here, here, and here.
Best times to visit Chicago:
I always say you survive the Chicago winters so you can enjoy the Chicago summers. While I would recommend visiting Chicago anytime of the year I would say visiting in the summer months will let you see all the city has to offer.
Some major events that frequently bring visitors to the city include St. Patricks Day Weekend, International Mr. Leather (gay event), Chicago Pride, Lollapalooza, Market Days (gay event), ARC Music Festival,
Getting to Chicago by Air:
Air Travel: Chicago is home to two international airports
Chicago O’Hare International Airport (ORD) is one of the largest airports in the world and services most major US airlines including a hub for both United and American Airlines. It lies just 16 miles from downtown Chicago and boasts four terminals — three domestic (Terminals 1, 2 and 3) and one international (Terminal 5). I personally only fly in/out of O'Hare and recommend you do the same.
Chicago Midway International Airport (MDW) is a much smaller airport located in the south side of Chicago and is primarily operated by Southwest Airlines. It’s located only 11 miles from downtown Chicago.
Transportation to/from O’Hare and Midway
My preferred method of arrival/departure from the airport is by taking the CTA. At O'Hare the Chicago Transit Authority (CTA) Blue Line ‘L’ Train, runs 24/7. For Midway take the CTA Orange Line ‘L’ Train. See maps and fares and my comments below on navigating the CTA. I usually feel safe on the CTA at all times but will Lyft and Uber late at night.
Lyft, and Uber pick-up points are available at both airports. 1-90 which takes you into the city is regularly backed up (especially during the day) so I would check Google Maps or Waze before booking. at O'Hare it takes about 10 minutes for Rideshares to leave the queuing area and pick you up so I suggest calling as you are walking off the plane/when you retrieve your checked bags.
Alternatively, you can e-hail and e-pay with CHICABS - approved apps ARRO and CURB. Credit cards are accepted in all taxis.
Numerous car rental companies have facilities at both O’Hare and Midway airports. My preferred rental car company is National. However, unless you plan on traveling to a distant suburb; I would not recommend renting a car for your visit.
Getting to Chicago by car:
Traveling in/out of the City: With Chicago being centrally located it makes a lot of sense to drive into the City for your visit. I would recommend having an electronic toll pass (iPass) to avoid unexpected missed toll fines and to save money at the tolls.
During your Visit: Once you're here I would recommend parking it and relying on walking, public transit, and rideshare services.
Parking:
View an interactive parking map of downtown Chicago to search for public parking lots and garages by address and points of interest.
To park at street meters I highly recommend downloading their App for ease of registration and monitoring your remaining time.
If you're an individual that I personally know I'm happy to give you 24 hour parking permits for my residential parking zone which is 383 which will allow you to park on the street where an open spot is available for free.
Getting Around Chicago - Public Transit:
About: Chicago's public transit system, including its iconic 'L' trains and extensive bus network, provides convenient and affordable 24 hour a day transportation option (trains and buses come less frequently during evening hours compared to commuting hours - plan your travels accordingly).
Paying for Travel: For short stays you can use Google Pay and Apple Pay to access our public transit network at the turn stile or bus entrance. For longer stays I'd recommend getting a Ventra Card because I think they make a great little souvenir.
Navigating the CTA: Navigating public transit in any city can be confusing. I recommend utilizing Google Maps for planning your trip and route. For accurate times of busses and trains I always refer to the Ventra App as sometimes Google Map's dosent have accurate live information.
Safety while using Chicago's Public Transit
Pay attention to your surroundings (.pdf).
Do not sleep on the bus or train, or become too engrossed in a book/mobile device (.pdf).
Keep personal audio devices/headphones at a low volume at all times.
Getting Around Chicago - Ride Shares:
Lyft and Uber are available to you at any time for a relatively reasonable price. There is sometimes surge pricing during peak times but it's relatively negligible. For more cost effective fairs I often do book a "wait and save option' in my experience it's a 50/50 chance if it comes sooner.
Curb provides you with access to digitally call a Chicago Taxi. This is a great way to get where you're going and avoid surge pricing. Just be prepared for a slightly sketchy User Experience and make sure you have your plan for payment all figured out.
Getting Around Chicago - Divvy Bikes & Scooters:
Divvy is Chicago’s bikeshare system, with hundreds of stations and thousands of bikes and scooters across Chicagoland for your use 24/7. Lyft has a partnership to administer and facilitate the bikes so all you need is the Lyft App to pick-up a bike or scooter. Please make sure you review Illinois bike laws before getting started.
Choosing your Accommodations:
I find choosing your accommodations to be quite a personal experience based on both personal preference and willingness to spend. While Airbnb is always a viable option for your visit I won't include specific recommendations as I've always found them to be more expensive than a traditional hotel, come with added fatigue in the experience, and unintended economic and societal consequences on the communities they operate in. As a result of this, and my large bias to Marriott and Hyatt, I've included some of my preferred properties in Chicago.
Hostels:
Freehand Chicago: I've stayed here on my first solo visits to Chicago and really enjoyed it. They have free breakfast and a moody lounge area located right in the middle of the River North Neighborhood.
Chicago Getaway Hostel: A hostel that seems to have a large population of international patrons.
Economical Hotels: I define economical as the hotel properties I've historically found the cheapest stays at compared to the market rate.
Preferred Hotels: These are the hotels I genuinely recommend and would stay if I was visiting Chicago.
W Chicago - Lakeshore: A Marriott property located in the River North neighborhood these rooms are modern, well designed, and the property has easy access to Lakeshore Drive and walking throughout downtown and the lake.
The Westin Michigan Avenue Chicago: A Marriott property located right on Magnificent Avenue in the heart of the shopping district. Rooms are clean and well kept. There can sometimes be loud noises coming from the street late at night you can hear in the rooms.
The Thompson Chicago: A Hyatt property with great rooms and convenient location in River North. This is where I choose for my parents to stay when they are visiting.
Hotel Zachary, Chicago, a Tribute Portfolio Hotel: A Marriott hotel located directly across from Wrigley Field in the Lakeview neighborhood. I recommend checking out this property if your itinerary depends on mostly being in the Lakeview neighborhoods. This property has a wide price range dependent on the Cubs game schedule.
Luxurious Hotels: These are hotels for individuals who want to splurge and I would love to come visit during your stay at any one of these properties.
Please note: If you're an individual I personally know I'm always willing to help book your stays at Marriott and Hyatt. Don't hesitate to reach out.
Neighborhood Guide
Chicago's neighborhoods are as diverse as they are distinct, each offering its own blend of culture, history, and character. While you should certainly explore as many of the neighborhoods in the city as they are all unique I spend most of my time in West Loop, River North, Lincoln Park, Lakeview (where I reside), Andersonville, and Logan Square.
During the summer months there is always various festivals, events, street takeovers. A quick google search and you can find something to do in the city.
I want to outline some of my favorite places in the Lakeview Neighborhood:
Chicago Diner: Indulge in innovative and mouthwatering vegetarian and vegan cuisine at the iconic Chicago Diner, where comfort food classics get a plant-based twist.
Uncommon Ground: Experience farm-to-table dining at its finest at Uncommon Ground, where locally sourced ingredients shine in creative and seasonal dishes.
Wangs: Satisfy your cravings for Asian-inspired comfort food at Wangs, where crispy wings, flavorful bao buns, and inventive cocktails take center stage.
Buzzed: Quench your thirst and indulge in artisanal cocktails at Buzzed, a cozy neighborhood bar serving up creative libations and a laid-back atmosphere.
Ann Sather Restaurant: Dive into hearty and delicious Swedish-American fare at Ann Sather Restaurant, known for its legendary cinnamon rolls and savory brunch options.
ROCKS Lakeview: A popular neighborhood burger and beer restaurant. One of my Dad's favorite places.
PingPong: Enjoy a lively dining experience at PingPong, where delectable dim sum, flavorful dumplings, and traditional Chinese dishes are served in a vibrant setting.
Eggsperience: Start your day right with a delicious breakfast or brunch at Eggsperience, where classic and creative egg dishes are served alongside hearty options to fuel your day.
CRAM Fashion: Explore the latest trends and unique finds at CRAM Fashion, a boutique offering curated collections of stylish clothing, accessories, and gifts.
Food
(*) Longman and Eagle Delicious “new american” michelin star restaurant that isn’t insanely expensive (~$15-30 entrees) - if we were to recommend one restaurant to go to in Chicago, this would be it
(*) Lula cafe Fresh, seasonal, very vegan and veg friendly (though they also have meat), Awesome brunch
Antique Taco Delicious, casual but upscale mexican with great decor and friendly staff
Owen & Engine Delicious burgers and other pub food
Calumet Fisheries Hole in the wall fish shack almost to the border of Indiana
(*) Publican Quality Meats Freshest meat you’ll find, basically an eat-in butcher
(*) Little Goat Diner Diner food with a fancy spin
The Promontory Hyde Park dinner spot and concert venue - ask for the chickpea fries even if they aren’t on the menu
Irazu - Costa Rican food with a casual vibe. BYOB
Antique Taco - tasty tacos with a fancy spin
90 Miles Cuban Cafe - Cuban food with a casual vibe. BYOB
En Hakkore and En Hakkore 2.0 - health bibimbap and sushiritos, respectively
Dusek’s & The Punch House Awesome pub attached to Thalia Hall (great shows) with a downstairs bar. Reliably delicious.
(*) Dove’s - elevated Tex-Mex.
(*) Reno - simple pizza (night) and bagels (morning). Delicious, cash only.
El Milagro - classic, delicious, cheap mexican in Pilsen
Taste of Lebanon - Cheap, delicious mediterranean from the kind of people who will save your tesla keys for you (long story). Go across the street to Middle East grocery & bakery for great grocery staples and their schwaffle wrap (the rest of the food is good but value is better at Taste of Lebanon)
Del Seoul - Korean fusion with delicious hot stone bowl bibimbap
Americano 2211 Fresh and delicious food, super nice staff, and a back garden that you’ll want to sit in for hours (also good cocktails)
Coalfire pizza Best woodfired, thin crust pizza with super fresh ingredients (and super fast service!)
Handlebar A vegetarian favorite! Delicious and creative vegetarian food, posters on the walls, heavily tattooed staff, loud music
Chicago Diner A vegan favorite! Diner style, vegan comfort food. The best milkshake in town (you would never know they are vegan)
Nookies Classic diner, multiple locations, breakfast all day!
5 Rabinitos Amazingly delicious Mexican food in Pilsen
Kie-Gol-Lanee - delicious Oaxacan Mexican food. Tragically no longer BYOB, but still make excellent margaritas.
Alice & Friends Vegan Kitchen - great vegan food and good for anyone with any sort of food allergies, typically Asian inspired cross over vegan dishes
Nebeb Ethiopian (formerly Ras Dashen) - our favorite Ethiopian in the city
Dessert
(*) Bang Bang Pie Small pie shop with a great back garden (also biscuits and potpies)
Hoosier Mama Pie Classic, delicious pie
Blackdog Gelato Delicious, creative flavors, only open in the summer until they run out!
(*) Floriole A delicious bakery in general, but most importantly, the maker of natasha’s favorite cookies ever (not a statement made lightly) - get the flourless chocolate hazelnut cookies before they sell out!
Lost Larson - delicious brother/sister owned bakery and a lovely place to sit inside on a chilly or rainy day
BYOB heaven: note the Chicago restaurant phenomenon of BYOB (most without any corkage fees), which someone once described as “feeling like you’re a part of a secret club that you didn’t do anything to get into” - bring your favorite drinks from a neighborhood liquor store and enjoy!
Drink
Coffee
Ipsento 606 Right on the 606 park with coffee in the morning and cocktails at night (also a good working spot during the day)
Star Lounge Funky/Hipster-y coffee spot with amazing coffee
La Colombe Classic and classy (no WiFi, good if you need no internet working time)
Intelligentsia Chicago classic
Phlour is a solid option in Edgewater
Cocktails/Beer/Kombucha
Violet Hour Intimate, dark, velvet curtained “hidden” bar with delicious cocktails
Scofflaw Fun cocktails, free warm cookies at midnight!
Map Room Huge beer selection, chill vibe
The Whistler Bartenders with long beards, some dancing, a back patio, and delicious drinks
Billy Sunday Dark, with draft cocktails and tasty snacks like fried chickpeas, borderline pretentious but not
Hopleaf Giant beer menu, good laid back vibe
The Northman Cider bar with a menu that’s probably 100 pages worth of cider
The Kombucha Room Kombucha on tap, 20 rotating flavors from local places in the midwest
Inner Town Pub Classic chicago neighborhood dive bar
The Aviary Fancy pants cocktails with smoke that cost $25+
Koval Distillery Local distillery with tours and tastings
Revolution Brewery Local brewery with tours and tastings (also has another location that’s a brewpub)
Attractions and Activities
Five Things You Can't Leave Without Doing:
Architectural Boat Tour: Experience the city's world-renowned architecture from the unique perspective of the Chicago River. These boat tours offer fascinating insights into the history and design of iconic buildings like the Willis Tower, Tribune Tower, and Wrigley Building.
Indulge in Deep-Dish Pizza: Treat yourself to a slice of Chicago's famous deep-dish pizza, characterized by its thick crust, generous layers of cheese and toppings, and hearty tomato sauce. Sample this iconic dish at legendary pizzerias like Lou Malnati's, Giordano's, or Pequod's Pizza.
Explore Millennium Park: Spend an afternoon exploring Millennium Park, home to the iconic Cloud Gate sculpture (affectionately known as "The Bean"), Crown Fountain, and Lurie Garden. Take a leisurely stroll, snap photos against the backdrop of the city skyline, and immerse yourself in art, nature, and culture.
Visit The Art Institute of Chicago: Delve into one of the oldest and largest art museums in the country, featuring a vast collection of masterpieces spanning thousands of years and cultures. Highlights include works by renowned artists such as Grant Wood, Edward Hopper, and Vincent van Gogh.
Explore Lakefront Trail: Take a scenic bike ride or leisurely stroll along the Lakefront Trail, stretching for 18 miles along the shores of Lake Michigan. Enjoy stunning views of the lake, beaches, parks, and skyline while soaking up the beauty and tranquility of Chicago's waterfront.
Iconic Tourist attractions to checkout while you're here:
Millennium Park: Explore this urban oasis featuring the famous Cloud Gate sculpture (affectionately known as "The Bean"), Crown Fountain, Lurie Garden, and outdoor art installations. If visiting in the summer months checkout the event schedule.
The Art Institute of Chicago: Wander through one of the oldest and largest art museums in the United States, housing a vast collection of renowned artworks spanning thousands of years and cultures. I'm a member of the Art Institute and if you're an individual I personally know reach out and I'm happy to take you there.
Museum of Contemporary Art (MCA): Delve into the world of contemporary art at the MCA, showcasing thought-provoking exhibitions and cutting-edge works by emerging and established artists. I'm also a member of the Museum of Contemporary Art and if you're an individual I personally know I'm happy to help arrange your visit.
Navy Pier: Experience Chicago's lakefront playground with attractions like the Centennial Wheel, Chicago Children's Museum, IMAX theater, and a variety of dining and entertainment options. They have fireworks every Wednesday and Saturday nights during the summer.
Willis Tower (formerly Sears Tower): Soar to the top of this iconic skyscraper for breathtaking views of the city skyline from the Skydeck's glass-floored observation deck.
The Magnificent Mile: Stroll down Michigan Avenue, known as the Magnificent Mile, for premier shopping, dining, and architectural landmarks including the historic Wrigley Building and Tribune Tower.
Lincoln Park Zoo: Visit one of the oldest zoos in the country, located within the expansive Lincoln Park, featuring a wide array of animals, exhibits, and family-friendly attractions.
Museum Campus: Explore this scenic area along Lake Michigan, home to world-class museums including the Field Museum, Shedd Aquarium, and Adler Planetarium.
Chicago Riverwalk: Take a leisurely stroll along the Chicago Riverwalk, lined with restaurants, bars, public art installations, and stunning views of the city's iconic architecture.
Wrigley Field: Catch a baseball game at this historic ballpark, home to the Chicago Cubs and steeped in over a century of baseball lore and tradition.
Off-the-beaten-path attractions and activities
Interactive museums in Chicago (some of my favorite places to visit)
Color Factory: Immerse yourself in a vibrant wonderland of hues and interactive art installations at Color Factory, where creativity knows no bounds.
WNDR Museum: Explore the intersection of art, science, and technology at WNDR Museum, where immersive exhibits invite visitors to question, play, and marvel at the wonders of the world.
Mindworks: Stimulate your mind and explore the mysteries of perception and cognition at Mindworks, where hands-on exhibits challenge your senses and expand your understanding of the human mind.
Museum of Ice Cream: Indulge your sweet tooth and dive into a whimsical world of ice cream-themed installations and interactive experiences at the Museum of Ice Cream, where every corner is a delectable delight.
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