I pour my heart into providing quality insights, and your support means the world to me. Welcome to the ultimate Chicago travel guide. This is all the essential information you’ll need for your trip to the Windy City.
Overview | Arriving in Chicago | Getting Downtown | Local Cell Service | Best Neighborhoods to Stay
Top Museums | Sports Stadiums | Theater & Comedy | Outdoor Actitivies | Shopping | Dining
Annual Events & Festivals | Best Time to Visit | What to Pack for Chicago | Day Trips & Excursions | Free Walking Tours
Overview
Chicago was discovered in the late 1600s by French explorers led by René-Robert Cavelier, Sieur de La Salle, who traveled down the Illinois and Mississippi Rivers.
They encountered the native Miami and Illinois tribes, who had long inhabited the region. The name “Chicago” comes from the native word “shikaakwa,” which means “wild onion” or “skunk.”
In the early 1800s, Chicago was a small trading post. It is because of the Chicago River that the city became a major transportation hub. Its location and transportation advantages would eventually lead to its growth as a major city and commercial center.
Chicago is an ideal tourist destination. From its deep-dish pizza to its world-class museums to its iconic architecture to its hip neighborhoods, there are plenty of reasons to visit Chicago.
So, whether you’re looking for a relaxing weekend getaway or an action-packed adventure, this ultimate guide will help you plan your trip and make the most of your stay.
In this guide, we’ll explore some of the city’s top attractions and things to do and uncover some of the best places to eat and drink in town. Ready?
Let’s go!
Arriving in Chicago
Direct Flights to Chicago
Several airlines offer direct flights to Chicago. There are two main airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). The most well-known airlines with direct flights are:
- American Airlines
- United Airlines
- Delta Air Lines
- Southwest Airlines
- Frontier Airlines
Airport Arrivals
Welcome to Chicago! Flight touchdowns are always a relief and it’s exciting to be on your way to experience the Windy City after a long journey!
If you arrive from another country, you’ll clear immigration and customs if needed. Next, you’ll need to go to the lower levels to pick up your luggage if you checked bags.
Getting Downtown
Ride-sharing services are on the same level as baggage claims for both airports. If you have arranged for pick up (eg. taxi, Lyft, Uber), make sure you note the door you are exiting because the service may ask you to meet at a specific exit.
➤ Read the Full Article: Easy Guide: 4 Ways to Get from the Airport to Downtown Chicago
Transfer services are available at either airport, but you must make reservations in advance. It’s easy to get downtown, but with many people arriving simultaneously, it can be a pretty busy line for taxis. Traffic can be terrible at peak periods or in inclement weather.
You can pre-book a transfer service to make your journey more comfortable after a long flight. Drivers will have nameplates with your details when they pick you up at the airport. After you collect your luggage, you will take a brief walk to the car, and your driver will take you to your destination.
➤Book a transfer service to enjoy a comfortable and hassle-free journey while visiting Chicago.
Rental Cars
You may wonder if you need a car in Chicago. The answer is no, unless you plan to explore the outer parts of the city that are not easy to access via public transportation. By eliminating car rental and parking fees, you can save some dollars during your stay.
However, to rent a car, you must present your reservation, driver’s license, and proof of insurance.
➤Touch down and take off with ease! Find your airport rental car!
Car Rental Insurance
Check to confirm that a rental car is covered under your car insurance; otherwise, you’ll need to purchase it from the rental agency to protect yourself from financial burdens in the case of an accident.
Driving to Chicago + Tolls
When visiting Chicago by car, you will learn that three expressways intersect with the city and depending on your destination outside of the city limits, you may be required to pay tolls.
- I-290 is an interstate highway that runs east to the Chicago Loop
- I-55 is a highway that runs in a northeastern direction to Chicago
- I-90 is an interstate highway that runs east and west to and from Chicago
Illinois has eliminated cash tolling. So the options for paying tolls are to use Pay-by-Plate, E-ZPass, or I-Pass.
The Pay-by-Plate online platform allows you to pay tolls without a transponder, which is a great option for rental cars.
You will need to go to the Illinois pay-by-plate website, identify the car you were driving by the license plate, and then pay the tolls due.
I-PASS is a program that requires a transponder to be mounted on the inside of your car. When you pass through the toll area, the tolls are paid electronically from the balance on your I-PASS account. The transponder can also be used with rental cars, or you can elect to use a transponder that the rental agency provides.
If you already have a transponder, it may be used within Illinois if it is part of the E-ZPass group that is comprised of 19 states:
| Massachusetts | New York | West Virginia |
| Minneapolis | New Hampshire | Kentucky |
| Illinois | New Jersey | North Carolina |
| Indiana | Rhode Island | Delaware |
| Ohio | Maine | Georgia |
| Pennsylvania | Maryland | Florida |
| Virginia |
Once you have reached the city, you can find available parking garages using Spothero.com or a hotel garage.
Use our guide to discover how easy it is to get around Chicago on foot and by using public transportation (this is a must-read!). This resource explains the various public transportation options and their costs. We also share some tips for driving in Chicago.
Local Cell Service
Staying connected with family and friends is one of several international travel essentials if you are traveling from another country.
We recommend a local SIM card for affordable data, voice, and text plans. Make sure your phone is unlocked and can accept SIM cards from different carriers.
➤ Buy a local SIM Card and stay connected!
Use message apps, like WhatsApp or Rakuten Viber, to help you stay in communication with those in your travel group.
Best Neighborhoods to Stay
Lincoln Park | Fulton Market (West Loop) | Downtown (The Loop)
River North | Streeterville | Wrigleyville | Magnificent Mile | The Gold Coast
Chinatown | Old Town | Wicker Park | Buck Town
If you’re wondering where to stay in Chicago, it depends on what you’re looking for.
Want to know where to stay in Chicago with kids? Lincoln Park might be your best bet – it’s got that family-friendly vibe and you’re close to the zoo.
Wondering where to stay for the first time in the Windy City? I’d suggest staying downtown in the Loop or maybe River North. You’ll be right in the heart of things, perfect for hitting all the major sights.
Now, if you’re trying to figure out where to stay in Chicago without a car, don’t sweat it. The Loop, River North, or even Streeterville are all super walkable, and you’ve got great public transit options. Plus, you’re close to everything, so you won’t miss having wheels.
View the highlights for each neighborhood along with a hotel recommendation. You’ll get picks from me, a local, on where I would book a staycation and why.
Just remember, wherever you end up, you’re in for a treat because each Chicago neighborhood has its unique flavor!
Read Posts
About Neighborhoods!
Lincoln Park:
- Location: North side of Chicago, bordering Lake Michigan
- Vibe: Refined. Family-friendly culture with affluence
- Known For: DePaul University, extensive parkland, upscale shopping on Armitage Avenue
- Attractions: Lincoln Park Zoo, Lincoln Park Conservatory, Chicago History Museum
- Where to Stay: The Neighborhood Hotel | Villa D’Citta
🏆 The Neighborhood Hotel
This hotel had me at electric kettles, it’s essential for morning coffee or tea. The interior reminds me of my first Chicago apartment more than a hotel, which adds to the experience of living like a local.
Lincoln Park has tons of options for family-friendly fun, nightlife, shopping, and dining. The premium bedding sounds like a traveler’s dream.
Fulton Market (West Loop):
- Location: Just west of downtown
- Vibe: Trendy. A former industrial area turned foodie paradise
- Known For: Restaurant Row on Randolph Street, Google’s Midwest headquarters, trendy loft conversions
- Attractions: Randolph Street Market, The Aviary, Rooftop Cinema Club, PunchBowl Social
- Where to Stay: Nobu Hotel | The Hoxton Hotel | The Emily Hotel | SoHo House Chicago | Homewood Suites by Hilton
🏆 The Emily Hotel
This upscale hotel is perfectly located in the Fulton Market neighborhood where I can dine al fresco, on the rooftop, or near a firepit. There’s a rooftop cinema that is perfect for date night. The interiors are spacious and modern. It’s an easy stroll to the Chicago Riverwalk, Michigan Avenue, or a nearby neighborhood like River North.
Downtown (The Loop):
- Location: Central business district
- Vibe: Dynamic. The bustling, urban core of the city
- Known For: Chicago Theatre District, State Street Shopping, Prohibition-era Financial District
- Attractions: Millennium Park, Art Institute of Chicago, Skydeck Chicago, The Money Museum
- Where to Stay: The Chicago Athletic Association | Palmer House by Hilton | The Pendry | Renaissance Chicago
🏆 The Chicago Athletic Association
The Chicago Athletic Association is one of the city’s best gems. It’s located on Michigan Avenue, close to top attractions like the Art Institute of Chicago, Millennium Park, and Cloud Gate. I love it because the building’s architecture and history are unique. Even the furnishings are from a bygone era. I also love the convenience of Cindy’s Rooftop for evening cocktails and great food while overlooking Millennium Park.
River North:
- Location: North of the Chicago River, west of Michigan Avenue
- Vibe: Lively. Artsy area that is also a nightlife hub
- Known For: Gallery district, upscale dining, nightclubs, Merchandise Mart
- Attractions: Chicago Riverwalk, Merchandise Mart, House of Blues
- Where to Stay: The Langham | Embassy Suites | Freehand Chicago | Fairfield Inn & Suites | SpringHill Suites
🏆 Embassy Suites
Embassy Suites has always been a great value hotel, and my last staycation here was a wonderful experience. It’s close to the Magnificent Mile, Chicago River (for an architectural boat tour), and museums.
The hotel amenities are great. There is a hot, made-to-order breakfast buffet to start your day. After exploring the city, wind down at the manager’s reception with a complimentary beverage and snacks. The rooms are spacious and equipped with a mini-fridge and microwave. It’s perfect for families with kids or teens.
Streeterville:
- Location: East of Michigan Avenue, along the lakefront
- Vibe: Cosmopolitan. Dense, urban, mix of residential and commercial
- Known For: Navy Pier, Northwestern Memorial Hospital, shopping along Michigan Avenue
- Attractions: Navy Pier, Museum of Contemporary Art, Oak Street Beach
- Where to Stay: Loews Hotel | Hyatt-Centric Chicago | Ivy Boutique Hotel | Sheraton Grand Hotel | DoubleTree by Hilton
🏆 Ivy Boutique Hotel
This hotel has modern, spacious rooms with a luxurious feel. The suites look particularly impressive, with separate living and sleeping areas, two TVs, and a large bathroom featuring a rainfall shower and soaker tub. The lobby and rooms are aesthetically pleasing, giving an upscale apartment vibe.
The location is perfect for exploring the Water Tower, Eataly, and the shops at Northbridge.
Wrigleyville:
- Location: Part of the Lakeview community area, on the north side
- Vibe: Energetic. Sports-centric, youthful
- Known For: Wrigley Field (home of the Chicago Cubs), sports bars, live music venues
- Attractions: Wrigley Field, Gallagher Way, Cubby Bear
- Where to Stay: City Suites | Hotel Versey Days Inn | Best Western Plus Hawthorne Terrace | The Chicago Hotel
🏆 Bestern Western Plus Hawthorne Terrace
I love the cozy setting in the courtyard. I can see myself sipping wine as the sun sets. The walk to Wrigleyville, the CTA, and the Lakefront is less than 15 minutes. The Laugh Factory is a 10-minute walk from the hotel and would make a great stop for evening entertainment.
The hotel looks clean and comfy. The amenities include a fitness room with a hot tub, kitchenette, and free daily continental breakfast.
Magnificent Mile:
- Location: Section of Michigan Avenue north of the Chicago River
- Vibe: Upscale
- Known For: High-end retail, landmark buildings like the Water Tower, luxury hotels
- Attractions: 360 Chicago Observation Deck, Water Tower Place, Historic Water Tower
- Where to Stay: InterContinental Hotel | Chicago Marriott Downtown | The Peninsula | The Gwen | Omni Chicago Hotel | The Warwick Allerton
🏆 InterContinental Hotel
I have stayed here before and loved the amenities. The swimming pool is amazing, and the breakfast buffet is outstanding. The location is unbeatable and it’s easy to walk to the Loop or Navy Pier. There are plenty of nearby restaurants and shopping. If you’re looking for a luxurious stay in a prime location, this hotel is a winner.
Gold Coast:
- Location: North of Streeterville, along the lakefront and near Oak Street Beach
- Vibe: Luxurious. Known for its historic mansions, upscale shopping, and luxury living. It has a more residential feel compared to Streeterville
- Known For: Upscale shopping on Oak Street, historic buildings, and a variety of high-end dining options. It’s a prestigious area known for its affluence and exclusivity
- Attractions: Oak Street Beach, Original Playboy Mansion, Charnel House Museum
- Where to Stay: Millennium Knickerbocker Hotel | The Drake | The Four Seasons
🏆 The Four Seasons
When money is no object, The Four Seasons is hard to beat. This 5-star gem offers an experience that’s worth every penny. The service is impeccable – the staff anticipates your needs before you even realize them. The full-service spa is a slice of heaven. The rooms are spacious and beautifully appointed, with stunning views of Chicago’s skyline or Lake Michigan. And there’s a rooftop pool!
Chinatown:
- Location: Southside, centered around Cermak and Wentworth.
- Vibe: Cultural enclave, tourist attraction.
- Known For: Chinese restaurants and various regional cuisines, shops, Chinatown Square
- Attractions: Chinatown Gate, Nine Dragon Wall, Ping Tom Memorial Park
- Where to Stay: Jaslin Hotel | SpringHill Suites Chinatown
🏆 SpringHill Suites
If you want to be right in the middle of this cultural hotspot, the choices are few. I would stay at the Springhill Suites because it’s an excellent choice for families. Located on Wentworth, which is one of the main streets in Old China Town, I’ll have dim sum and boba tea right at my fingertips.
Wicker Park:
- Location: Situated northwest of downtown Chicago.
- Vibe: Edgy. Known for its hipster culture, vibrant nightlife, and artistic scene.
- Known For: Features vintage shops, music venues, trendy bars, and restaurants. It’s a popular area for young professionals and artists.
- Attractions: The 606, Wicker Park, Flat Iron Arts Building
- Where to Stay: Wicker Park Inn | The Robey
🏆 The Robey
Both hotels are within a 10-minute walk of the CTA Blue Line (Damen station). I would stay at the Robey if it was a family staycation. The accommodation is spacious, and we would enjoy the rooftop terrace and pool. It’s a great area to explore the neighborhood. Sultan’s Market has great food and is just a 3-minute walk from here.
However, if I were by myself or with a girlfriend, I would stay at the Wicker Park Inn for the quaint and cozy spaces.
Old Town:
- Location: Located north of downtown Chicago, near the lakefront.
- Vibe: Quaint. Known for its historic charm and architecture.
- Known For: Home to the famous Second City comedy club, Victorian-era buildings, and a variety of boutique shops and eateries. The atmosphere is more relaxed and quaint compared to Wicker Park.
- Attractions: Second City, Old Town Art Fair, St. Michael’s Church
- Where to Stay: The Sono Chicago | Hotel Lincoln
🏆 The Sono Chicago
I love the light and airy feel of these spaces. The Sono is near Michigan Avenue and Lincoln Park Zoo, so family outings will be a breeze at this urban accommodation. There is a free continental breakfast, a rooftop terrace, and a fireplace in the lobby, which begs me to sit close with a good book.
Bucktown:
- Location: Northwest of downtown, part of the Logan Square community
- Vibe: Eclectic. Artsy, gentrifying
- Known For: Galleries, boutiques, trendy restaurants, The 606 Trail (an elevated park)
- Attractions: The Map Room, Club Lucky, Bucktown Farmers Market
- Where to Stay: The Hotel at Midtown | Ray’s Bucktown Bed & Breakfast
🏆 The Hotel at Midtown
It’s hard to believe this gem is in the middle of Chicago. From the fitness facilities to the yoga room, the decor and architectural elements are incredibly imaginative. There’s an indoor/outdoor seasonal pool and a hot tub! The perks at this hotel are insane—pilates classes, an on-site spa, tennis courts, and supervised childcare!
Top Chicago Museums
Best Museums in Chicago
Museums are a great way to spend a day when visiting Chicago, especially when you need rainy-day activities. Visiting museums can be educational, entertaining, and even inspirational.
The acclaimed Art Institute of Chicago is among the world’s most esteemed museums, boasting one of the planet’s premier collections of Impressionist, Modern, and Contemporary art.
Best Art Museums in Chicago
Best History Museums in Chicago
- DuSable Black History Museum and Education Center | 740 E 56th Pl
- The Field Museum of Natural History | 1400 S DuSable Lake Shore Drive
- Medieval Torture Museum | 177 N State St
- Chicago History Museum | 1601 N. Clark St
- National Hellenic Museum | 333 S. Halsted St
- Chicago Sports Museum | 835 N. Michigan Ave
- Jane Addams Hull-House Museum | 800 S. Halsted St
- Pritzker Military Museum & Library | 104 S. Michigan Ave
- Ukrainian National Museum | 2249 W Superior St.
- Clarke House Museum | 1827 S Indiana
- Swedish American Museum | 5211 N. Clark St
Read Posts About
Chicago Museums!
Most Popular Outdoor Activities
Millennium Park
This is Chicago’s award-winning public park located in the heart of downtown. You will love the expansive acreage of green space and gardens, which are great for strolling. Spending time outdoors in the large green spaces is a great way to relax and unwind when visiting Chicago.
From art installations, summer concerts, and interactive programs to ice skating, biking, and running trails, Millennium Park has something for every season.
If you’re looking for a fun day out with friends or family or just want to relax in the sun, add Millennium Park to your itinerary.
Navy Pier
How about 3,300 feet of pure fun on the lake? Navy Pier is very popular for visitors and locals. The pier has multiple levels and sections that will pique your interest both indoors and outdoors.
From boat rides and sightseeing tours to shopping, dining, entertainment, theater, amusement rides, or just people-watching, there are lots of ways to experience the pier when visiting Chicago.
You can also rent bikes for a lakefront ride, take an evening dinner cruise out with friends, or for a romantic evening.
Chicago Riverwalk
The Riverwalk is a beautiful public space located along the banks of the Chicago River.
It is a popular destination for locals and visitors because there are a variety of activities and attractions to explore.
You can rent electric boats, go kayaking, see art exhibits, and enjoy outdoor dining with live music.
The Riverwalk has a nice view of Lake Michigan on the east end, Adirondack chairs to relax on the west end, and lots of bars and restaurants in between.
The Lakefront Trail
This scenic 18-mile path runs along the shoreline of Lake Michigan. It’s the perfect place to get away from the hustle and bustle of city life and take in some fresh air when visiting Chicago.
You can explore nature at its finest with stunning views of the lake, take in some culture at one of the Chicago museums and attractions, or simply relax with a picnic on one of its many beaches.
Outdoor lovers can also enjoy a few hiking trails near Chicago. The 606, or Bloomingdale Trail, is also great for walking, jogging, and biking.
Chicago Sports Stadiums
Chicago has a die-hard sports scene with passionate fans. Along with professional teams in baseball, football, basketball, and hockey, the city also hosts minor league and college sports events. Fans of these teams can be found cheering them on throughout Chicagoland during their respective seasons.
Read Posts About
Chicago Sports!
Wrigley Field
📍1060 W. Addison St.
- Chicago Cubs – Major League Baseball
- How to get there: From downtown, take the CTA red line and head north, exit at Addison station.
United Center
📍1901 W Madison St
- Chicago Bulls – National Basketball Association
- Chicago Blackhawks – National Hockey League
- How to get there: From downtown, take the CTA green line and head west, exit at Damen station (currently under construction). Then walk south to the stadium.
➤ Find tickets to see your favorite Chicago team!
Soldier Field
📍1410 Special Olympics Dr
- Chicago Bears – National Football League
- Chicago Fire FC – Major League Soccer
- How to get there: From downtown, take the CTA bus #130 to the museum campus.
Guaranteed Rate Field
📍333 W 35th St
- Chicago White Sox – Major League Baseball
- How to get there: From downtown, take the CTA red line and head south, exit at Sox-35th Street station.
Wintrust Arena
📍200 E Cermak Rd
- Chicago Sky – Women’s National Basketball Association
- How to get there: From downtown, take the CTA green line and head south, exit at Cermak-McCormick Place station. Then walk about 6 minutes to the arena.
The city also boasts two Major League Soccer clubs: the Fire and Red Stars. It’s also easy to catch games at a university if you are visiting alumni. There are also plenty of amateur and recreational sports leagues for those who enjoy playing themselves.
Attending a sports game is a great way to experience Chicago’s sports culture, soak up the atmosphere, and cheer for your favorite team when visiting Chicago.
Theater & Comedy
There’s something about seeing a live performance that just can’t be beaten. I’ve been to a few different theaters in the city, but my favorite has to be the Chicago Theater. There’s just something about this historic spot with the iconic Marquis.
The theater district is bustling with arts and performances, and you’ll be able to see a variety of shows during your stay. From Broadway musicals to local productions, you’ll find that the small theater performances are surprisingly well-done.
Theatre Venues
- Goodman Theatre | 170 N. Dearborn St
- Auditorium Theatre | 50 East Ida B. Wells Drive
- Lookingglass Theatre Company | 821 Michigan Ave
- Victory Gardens Biograph Theater | 2433 N Lincoln Ave
- Theater on the Lake | 2401 N Lake Shore Dr
- Steppenwolf Theatre | 1650 N Halsted St
- Victory Gardens | 2433 N Lincoln Ave
Broadway in Chicago
- Nederlander Theater | 24 W. Randolph
- Cadillac Theatre | 151 W. Randolph
- CIBC Theater | 18 W. Monroe
Comedy Clubs
- Zanies | 1548 N Wells St
- The Second City | 230 W. North Ave
- The Laugh Factory | 3175 N. Broadway
You will also be particularly impressed with the level of talent on display. The acting, singing, improv, and dancing are all top-notch, and you’ll enjoy every minute of the experience.
If you are short on time while visiting Chicago, I highly recommend The Second City just for the experience of being at an iconic comedy club that has launched the careers of many comedians who appeared on Saturday Night Live.
➤ Find tickets for a fun night out on the town!
Every February, Chicago hosts Theater Week where you can attend performances at a reasonable value. If you’re looking for an exciting theater scene, definitely check out Chicago’s theater district. You won’t be disappointed!
There is no shortage of places to shop while visiting Chicago! You can find great retail therapy in the various neighborhoods and do some serious shopping, and let me tell you, it will be a blast!
Start on Michigan Avenue, where all the high-end stores are located. It is so much fun trying on clothes and picking out new outfits.
Next, head over to State Street, where there are tons of great shops and boutiques. You’ll spend hours browsing and will find some amazing deals on clothes and jewelry. You can even grab a few souvenirs for friends and family back home.
➤ Discover tips on where to get Chicago souvenirs!
- Magnificent Mile | Between Chicago River and Oak Street
- State Street | Between Adams and Lake Street
- Block 37 | 108 N. State St.
- The Shops at North Bridge | 520 N. Michigan Ave.
- The Water Tower Place | 835 Michigan Ave.
- 900 North Michigan Shops | 900 North Michigan Ave.
- Fashion Outlets of Chicago | 5220 Fashion Outlets Way, Rosemont
Whether you’re looking for designer duds on Michigan Avenue or bargains on State Street, Chicago is a shopper’s paradise. And with all the great restaurants and attractions nearby, it’s easy to make a day of it. There’s nothing like a shopping spree in the Windy City!
Indoor and Outdoor Markets
- Chicago French Market | 131 N Clinton St | Monday–Friday from 7AM to 7PM, Saturday 9AM-4PM
- Randolph Street Market | 1341 W Randolph St | Saturday–Sunday from 10AM to 5PM
- Maxwell Street Market | 800 S Desplaines St | Last Sunday of the Month from 7AM to 2PM
Dining
The food scene in Chicago is nothing short of epic. Read these posts for tasty adventures!
If you love pizza, then you’ll want to check out some of the best places to enjoy it in Chicago. From deep dish to thin crust, you will find it is a unique Windy City experience! We’ve compared Chicago to NY-style pizza and listed the best spots for deep-dish or thin-crust pizza in Chicago.
If you’re visiting Chicago and looking for an amazing dining experience, you’ll want to check out some of the city’s top restaurants, including the Michelin-starred Alinea. Whether you’re looking for great Chicago breakfast spots, romantic dinner for two or a night out with friends, or plant-based restaurants, these spots are so chill and tasty.
So, without further ado, here are our picks for the best places to eat in Chicago!
Fine Dining
- Alinea | 1723 N. Halsted St
- Mastro’s | 520 N. Dearborn St
Casual Dining
- Time Out Market | 916 W Fulton Market
- The Purple Pig | 444 Michigan Ave
Romantic Restaurants
- Geja’s Cafe | 340 W Armitage Ave
- Gibsons Italia | 233 N Canal St
Chicago Pizza
- Lou Malnati’s | 439 N Wells St (various locations)
- Giordano’s | 730 N Rush St (various locations)
- Pizano’s | 61 E. Madison (various locations)
- Pequod’s | 2207 N Clybourn Ave
- Gino’s East | 162 E Superior St
- Pizzeria Uno | 29 E Ohio St
Annual Events & Festivals
What I love most about Chicago is that it provides opportunities for people from different communities to come together and celebrate at any time of the year.
Chicago’s holiday celebrations are magical, from Christmas shopping to the Christkindl market. Here is our list of recommended festivals you should not miss when you visit Chicago. Be sure to book accommodation well in advance in peak seasons.
February
- Chicago Auto Show
- First Bites / Chicago Restaurant Week
March
- St. Patrick’s Celebrations & Dying the Chicago River
June
- Chicago Blues Festival
- Chicago Food Truck Festival
- Chicago SummerDance (thru September)
July
- The Taste of Chicago
- Pitchfork Music Festival
- Windy City Smokeout
August
- Lollapalooza
- Chicago Air & Water Show
- Bud Billiken Parade
- Ribfest Chicago
- Taste of Greektown
September
- Riot Fest
- Chicago Jazz Fest
- Lakeview Taco Fest
- Apple Fest
- Pilsen Mexican Independence Day Parade
October
November
- Chicago Christkindlmarket (thru December)
- Magnificent Lights Festival
Day Trips & Excursions
Feeling adventurous? Or perhaps you’re visiting Chicago again and you want to wander beyond the Bean? If you love to pack in as much as possible, then a day trip from Chicago may be just what you need. We have a list of places that will take two hours to five hours by car.
- Milwaukee, Wisconsin
- Union Pier, Michigan
- Frankenmuth, Michigan
- Holland, Michigan
- Indiana Dunes State Park – Northwest Indiana
- Galena, Illinois
- Oak Park, Illinois
- Starved Rock State Park – Oglesby, IL
- Lake Geneva, Wisconsin
- Garfield Park Conservatory, Chicago
- Door County, Wisconsin
- Michigan City, Indiana
The Best Time to Visit
Seriously, there is no wrong time for visiting Chicago because there are always iconic sights, colorful local culture, and must-sees to create an itinerary that will make your stay exactly what you need.
For the best weather conditions, we recommend visiting Chicago between April and June. If you are comfortable traveling in 90-degree temperatures, July and August are good months to visit Chicago, but you may want to add some lakeside activities to stay cool.
September through November are also good months for visiting Chicago. It borders the cooler season in Fall, but you will mostly avoid snowy weather.
December through February are the coldest months. Temperatures begin to warm in March, with occasional snow and rain. Knowing how to dress in Chicago in this transitional season can be tricky.
How Long Should You Visit
To see the top attractions while visiting Chicago, you should allow at least three days for your visit.
Most top Chicago attractions and architecture tours are 5 to 25 minutes apart, and when you factor in lunch and the sights, you can comfortably squeeze in two to four activities per day.
Of course, you’ll need to consider some factors when deciding how many days to stay in Chicago, such as where you want to go, what you want to do, and the pace at which you want to spend your days.
What to Pack for Each Season
When visiting Chicago in Spring and Autumn, clothing should be layered so that you can adjust for warmth throughout the day. Your base layer should be slightly fitted like a basic tee or long-sleeved top. The mid-layer should be thicker but non-restrictive — a hoodie or light sweater will work, just make sure it is breathable. Finally, the outer layer should be a heavier piece that complements your first two layers and brings the outfit together, like a pea coat or rain jacket.
Read the Full Article Now and Dress Like a Local!
When visiting Chicago in Summer, wear breathable clothing like cotton. Linen is also a good choice for staying cool, but it’s not one of the best wrinkle-free materials for travel. It’s easy to maximize outfits in summer by doubling up on the wear. Cargo pants and summer dresses are also great options for mixing and matching styles.
When visiting Chicago during the colder season, you need to be winter-ready. A coat, scarf, insulated gloves, and boots are essential for snowy and wet weather. Dress for warmth, because the “hawk” is real! If you arrive in Chicago from a warmer climate and don’t want to invest much money, you can try thrifting at a Chicago store.
Final Thoughts on Visiting Chicago
Chicago is one of the most vibrant cities in the United States. With its rich history and modern attractions, it’s no wonder why millions of people look forward to visiting Chicago each year.
Come for the iconic architecture and world-class museums, but stay for the community vibes, the food, and the culture.
Whether you’re visiting Chicago for a weekend getaway or an extended vacation, this guide will help you plan your trip and ensure you don’t miss out on anything!
During your visit, you can learn about Chicago’s history, discover why it’s such a great destination, and use these tips to make the most of your stay.
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