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Chicago Travel Guide | What to See, Eat and Drink

Chicago Travel Guide | What to See, Eat and Drink
Reading Time: 16 minutes

Updated: 12/26/2023 | Chicago Travel Guide

Wings of Mexico Statue Downtown Chicago Quince LInen Dress

Wings of Mexico (Downtown Chicago)

About Chicago

Chicago is a town bustling with energy and so many things to do. Even when the weather gets cold, Chicago still has a lot to offer year round. It’s a big city that’s not as crowded nor fast-paced as New York but still filled with more things to do than you’ll have time in a single visit.

Chicago is home to more than 2.7 million people, making it the third-largest city in the U.S. and the largest city in the midwest. It’s lined with urban beaches located along Lake Michigan and is known as the birthplace of the skyscraper. 

It’s endearingly nick-named Chi-town, the Windy Cindy (not because of the wind, but because of how politicians were easily persuaded with money), and the Second City (not because it’s second to New York, but because the city was actually built twice). A massive fire in 1871 destroyed much of the city center, leaving behind just a handful of structures and paving the way for Chicago to construct one of America’s tallest and most beautiful skylines.

Chicago also has a huge sports presence. With professional baseball, basketball, football, hockey, and soccer teams, Chicago is a sports lover’s dream come true. You can catch a Chicago Bears game at Soldier Field, a Cubs or White Sox ball game at Wrigley Field, a round of soccer with the Chicago Fire, the Bulls for a basketball game, or a Blackhawks game for hockey. 

Chicago is also a foodie destination, offering world-class museums, architectural gems, luxury shopping, and a bunch of live music venues, theatre, and comedy clubs. And if the band Chicago is your jam, you’re in the right place.

It’s a city with something for everyone! Just make sure you save some room for a beloved deep dish pizza and Chicago dog. You cannot miss these!

Below we’ll offer information and recommendations to help you plan for your visit to Chicago.

Best Time to Visit Chicago

Chicago summers can be beautiful but humid and winters can be long, windy, snowy, and brutally bone-chilling. Fall is typically pleasant with colorful fall foliage.

Below are Chicago’s average high and low temps for each month. Use this information to help you determine when you want to visit Chicago.

Month Avg Low Temp Avg High Temp
January 18 32
February 20 34
March 29 43
April 40 55
May 50 65
June 60 75
July 66 81
August 65 79
September 58 73
October 47 61
November 34 47
December 23 36

Thinking of heading to Chicago in the winter? Read our guide on how to survive a Chicago winter. We offer tips on how you should dress so that you can stay warm while exploring the city.

How to Get to Chicago

You can easily fly into any of these airports:

  • Chicago O’Hare International Airport (ORD) – The most popular airport with both domestic and international departures and arrivals. Many airlines connect in ORD because it is a hub for international connections.
  • Chicago Midway International Airport (MDW) – Second most popular airport but does not have as many connections and is a little further from downtown.
  • Chicago-Rockford International (RFD) – Most travelers ideally would not arrive or depart from this airport if their intentions are to visit downtown Chicago. RFD is located 85 miles northwest of Downtown Chicago.

Where to Stay in Chicago

  • Hilton Downtown – This historic hotel has been featured in the Home Alone movie and is located conveniently next to Grant Park. We stayed here during Lollapalooza and it was the perfect spot to head back to after a long day on our feet at the festival. We also booked with our Hilton Honors status and used the Amazon employee rate and received $54 in food and beverage credit and only paid around $165 per night. 
  • Thompson Hotel – Located just 5 minutes from the beach and central to many downtown Chicago attractions.
  • Langham – Centrally located in downtown Chicago.
  • Westin – Located on Michigan Ave near the Magnificent Mile and is a dog friendly hotel! We love the location and how dog friendly they were.
Bebot the dog at Westin on Michigan Avenue Chicago Illinois

Bebot the Dog in the Westin on Michigan Avenue

Hilton Downtown Chicago Grand Ballroom Lobby Quince Linen Dress

Hilton Downtown Chicago Hotel

How to Get Around Chicago

Train: The best way to get around Chicago is by train. The Chicago Transit Authority (CTA) will pretty much take you anywhere in Chicago proper. We highly recommend downloading the Ventra App where you can buy train and bus tickets and tap to use. You can also tap to pay using Google or Apple pay, but the costs will be a little more expensive than using the Ventra App.

Bus: The next best way to get around locally, is by bus. Use the Ventra App to purchase and utilize tap to pay when riding the bus. Bus schedules can be found by using Google Maps.

Walking: The second best way is by walking! Chicago is totally a walkable city as it’s very flat. There are some areas that you may want to avoid in the evening.

Bike/Scooter/Segway: Another fun way to get around town is by using recreational transportation. You can easily rent these items or book a tour and go with a guide to see the city.

Driving: You can drive around Chicago but parking is very expensive and there may be a lot of traffic during high season.

Uber/Lyft: Uber and Lyft are great ways to get around Downtown. Once you start to use these services to get beyond Downtown, it can get pretty pricey. Prices also seem to surge in the evenings.

What to Do in Chicago

See the Bean

The Bean (or Cloud Gate) is an iconic Chicago statue made entirely out of stainless steel and two metal rings.

The bean was designed by Indian-born British artist Anish Kapoor. It’s the centerpiece of AT&T Plaza at Millennium Park in the Loop area of Chicago, Illinois.

You didn’t really go to Chicago if you didn’t visit the Bean! It’s iconic!

Cloud Gate the Bean Chicago Illinois Schimiggy

The Bean!

Get the Best Views of Chicago

  • London House: Come to London House for the best view of the river and city. It’s located next to DuSable Bridge.
  • Signature room 96th floor: Go in for a drink or buffet brunch. No reservations are needed. Visit the women’s bathroom because it has the best views of the lake and city from the John Hancock Tower. 
  • There’s a picture spot across the street from the Apple store and in front of Trump Tower that everyone takes pics in front of. It has an awesome river and city view.

Wrigleyville (AKA Cubs Stadium)

Try to catch a Cubs game at Wrigley Field. I once watched the Cubs versus the White Sox and the crowds and bars were very lively! You’ll want to hang out and meet people in the bars afterward.

Magnificent Mile for shopping

The Magnificent Mile is a strip along Michigan Avenue that is known for its shopping. All the major brands, department stores, and high-end designers can be found here.

Magnificent Mile Shopping in Chicago Illinois

Luxury Mall on Magnificent Mile

Go Up Willis Tower

Willis Tower, previously known as Sears Tower, is a 110-story skyscraper that was the tallest building in the world for almost 25 years. It’s now the second-tallest building in the U.S. behind One World Trade Center in New York.

More than 1 million people visit the Willis Tower’s observation deck each year, making it one of Chicago’s most popular tourist destinations.

The Willis Tower observation deck is located on the 103rd floor of the building and now includes retractable glass boxes that extend four feet over the street below. On a clear day, visitors can see Michigan and Wisconsin.

Experience 360 Chicago

The John Hancock Building’s 360 Chicago observation deck is located 1,000 feet above the Magnificent Mile and offers 360-degree views of the Chicago skyline and Lake Michigan.

If you’re not afraid of heights, try the enclosed moving platform that tilts visitors over Michigan Avenue.

Also, enjoy a beverage at Bar 94, Chicago’s highest bar!

Check out our recap of our visit to 360 Chicago on Instagram.


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Visit Frank Lloyd Wright’s Houses and Buildings

Famed architect Frank Lloyd Wright came to Chicago in search of work in 1887. Throughout his career, Wright designed more than 1,000 structures, several of which are located in the Chicago area.

The most notable options for architecture geeks that are easily reachable by public transit include:

Stroll Through Grant Park

Grant Park is a 319-acre urban park situated along Lake Michigan in downtown Chicago. The park is often called “Chicago’s front yard” and includes the Art Institute of Chicago, Millennium Park, and the iconic Buckingham Fountain, which was featured in the title sequence of the TV show “Married… with Children” and the movie “National Lampoon’s Vacation.”

The fountain operates from 8 a.m. to 11 p.m. from mid-April to mid-October. Water shows are scheduled for every hour on the hour. Millennium Park is known for being the destination for summer concerts (such as Lollapalooza) and winter ice skating within Grant Park.

Buckingham Fountain Downtown Chicago travel guide

Buckingham Fountain

Visit the Chicago Theater

The Chicago Theater is a landmark that was built in 1921 and previously served as one of the city’s premier movie theaters. Nowadays, it hosts concerts, plays, touring Broadway shows, comedy, and more. The theater’s famous marquee (AKA the “Chicago sign”) is frequently used in movies, TV, and artwork depicting the city.

Can’t work a show into your Chicago itinerary? Tours of the property are also available.

Famous Chicago Theater Sign

Chicago Sign

Hunt for Public Statues

There are plenty of statues to see in Chicago. Aside from the famous Bean, here are a few that we highly recommend:

Unknown Statue by Picasso in Chicago Illinois

Unknown by Picasso

Monument with Standing Beast Statue by Jean Debuffet

Monument with Standing Beast

The Gentlemen Sculpture Downtown Chicago

The Gentlemen

Stroll Down the Riverwalk

The best place to start the Riverwalk is from the Franklin-Orleans Street bridge and start walking east. The Riverwalk will give you the best views of downtown Chicago. We typically end our walk at the Navy Pier.

Marina City aka the Corn Cob in Chicago Illinois

Marina City is located along the Riverwalk

Chicago Riverwalk View Schimiggy Alex Tran

Chicago Riverwalk

Take a Ride on a Water Taxi

Get around Downtown Chicago along the river via the Chicago Water Taxi service. These affordable boats will cost you only $6 one way and is a great way to see downtown from a boat along the Chicago River. 

It’s cheaper than their guided boat tours, which we think you should check out if you have time.

Take the Chicago Water Taxi

Visit the Navy Pier With Your Family

The Navy Pier is an amazing place for families! The Chicago Children’s Museum is located here and houses a lot of shops and restaurants that are great for shopping and dining.

We love the fun Centennial Ferris wheel! It’s great to ride and get a view of the Navy Pier from above as well as to take fun photos.

Related: Ferris Wheels from Around the World

The Offshore Rooftop just recently opened in 2021 at the Navy Pier! It has 360 rooftop views of the pier and an amazing view of Chicago’s Downtown skyline. Definitely make a stop here when you’re in town.

Centennial Ferris Wheel at Navy Pier in Chicago Illinois

Centennial Ferris Wheel

Float With Skydeck Chicago

The SkyDeck is located 103rd floor of the former Sears Tower and comes with clear observation boxes & views extending to four states (Illinois, Indiana, Wisconsin, and Michigan).

The visibility from the Skydeck is approximately 40-50 miles (or 65-80 kilometers).

Check out the Rookery Building

The Rookery was designated as a Chicago Landmark in 1972. The building was designed by famous architectural partners Burnham and Root and was originally completed in 1888.

Adding to its impressive stature, Frank Lloyd Wright redesigned the stunning two-story, sky lit lobby in 1905. The Rookery stands as one of the most highly recognized architectural creations in all of Chicago.

Adler Planetarium

The Adler Planetarium is the United State’s first planetarium and is great for those who have a love for all things space.

See Marine Animals at the Shedd Aquarium

The SHEDD Aquarium is a great place to see aquatic animals. They have over 32,000 aquatic animals to see!

Museum of Contemporary Art

The Museum of Contemporary Art houses a collection of modern art from all over the world. On Tuesdays, the museum is free for Illinois residents.

Museum of Contemporary Art MCA in Chicago Illinois

Museum of Contemporary Art (MCA)

Art Institute of Chicago

The Art Institute of Chicago (ARTIC) is another great destination for art lovers. Many art displays are created by students attending or who have attended the Art Institute.

You’ll also see famous artwork by Andy Warhol, American Gothic by Grant Wood, the Old Guitarist by Pablo Picasso, and much more.

Second City Comedy Show

Chicago is known as the Second City because it was built twice after burning down to the ground!

There is also another rumor that it is called Second City because it’s second to the biggest city in the United States of America, New York!

Second City Comedy Show is a venue in Chicago that offers musicals, plays, and improv shows and courses. If you’re a thespian, you may want to check out some shows at Second City!

Visit Wicker Park + Bucktown

Wicker Park and neighboring Bucktown are hipster havens known for their art, community, nightlife, and food scenes. Each neighborhood has a unique architectural style, and both are brimming with street art, bars, and restaurants. 

We love coming here for the street art including the Greetings from Chicago mural!

Greetings from Chicago Mural Schimiggy

Greetings from Chicago Mural Schimiggy

What to Eat in Chicago

  • 3 Arts Club Cafe – Come dine in this ornately decorated restaurant. The restaurant is located within the Restoration Hardware building where you can find a coffeehouse, wine bar, and American restaurant.
  • Al’s Beef ChicagoCome here for their Italian beef sandwiches, which are to die for. The meat is super beefy, so cut the flavor by adding toppings such as peppers, pepperoncini, and provolone cheese. Skip their hot dogs and get those at Portillo’s instead.
  • Alinea – Alinea is a three-star Michelin restaurant that’s become regular on lists of the world’s best restaurants. Chef Grant Achatz is best known for his avant-garde dishes that blend creativity and flavor into an unforgettable experience. A famous dish from their tasting menu is the edible helium balloon made from taffy.
  • Au Cheval – Au Cheval is known for their amazing burgers. They do not take reservations and work on a first come first serve basis. It’s best to visit during the week when lines are not as long.
  • Billy Goat Tavern – The Billy Goat Tavern was established in 1934 and has been a longtime Chicago institution. Founder William Sianis, a Greek immigrant,  bought the tavern (then called the Lincoln Tavern) with a $205 check that bounced. As told by Sianis, a goat fell off of a passing truck and wandered inside, inspiring him to change the tavern’s name to Billy Goat Tavern. You have to try their famous Cheezeborgers which were made famous by the “Saturday Night Live” (SNL) show.
  • Bub City – Come for good BBQ and their live country music at night and is conveniently located downtown. Get ready to feel like you’ve been transported to Nashville!
  • Duck Duck Goat – Sister restaurant of the Girl and the Goat. Located just down the street from the Girl and the Goat.
  • The Girl and the Goat – Girl and the Goat is the brainchild of chef Stephanie Izard, the first female chef ever to win Bravo’s Top Chef. Izard is a James Beard Award-winning chef and has beaten chefs including Bobby Flay in cooking competitions. Girl and the Goat feature family-style dishes with Meditteranean inspiration. Menu items include swiss chard-kale pierogis, grilled pork belly, wood oven-roasted pig face, and goat liver mousse. Don’t skip the handcrafted cocktails or the bourbon ice cream dessert. 
  • Gene and Georgetti’s – Come here if you’re a steak lover. Gene & Georgetti was founded by a pair of Italian immigrants in 1941 and is one of Chicago’s oldest steakhouses. Celebrities such as Frank Sinatra, Bob Hope, Lucille Ball, Keanu Reeves, and Will Ferrell are among the celebrities that have dined on its giant portions of steaks, chops, and classic Italian entrees.
  • Giordano’s – You can’t go to Chicago and not eat a deep dish pizza. Giordano’s is one of several pizzerias serving up the local delicacy and has 65 locations spread across the country. The restaurant traces its roots to a small northern Italian town where Mama Giordano made a popular Italian Easter Pie, the precursor to Giordano’s modern deep dish. 
  • Hampton Social – Cute spot for food and drinks!
  • Hubbard Inn – Cute dinner/drink spot located on Hubbard, a busy street for nightlife and debauchery.
  • JoJos Shake BAR for good desserts!
  • Le Colonial – A high-end Vietnamese restaurant with gorgeous decor that will make you feel like you’ve time-traveled to a tropical paradise. We love their Pho Hanoi, Banh Cuon (rice wraps), and Chao Tom (shrimp meatballs wrapped around a sugar cane). Reservations are required. 
  • Lou Malnati’s – Lou Malnati worked at Chicago’s first deep dish pizzeria in the 1940s then made his way to the suburbs to open a pizzeria of his own. Lou Malnati’s deep dish pizzas are made from scratch using hand-selected California vine-ripened tomatoes. Mozzarella is sourced from a small Wisconsin dairy farm that’s been supplying the restaurant for more than 40 years, and sausage is flavored with an exclusive — and secret — blend of spices. You need to try their BUTTER CRUST. It’s the reason why they’re famous.
  • McDonald’s Headquarters – Head over to their HQ office to enjoy their INTERNATIONAL menu! We are obsessed with McDonald’s and collect their Happy Meals when we travel internationally
  • Monteverde – A Michelin-starred Italian restaurant created by James Beard Award-winning Chef Sarah Grueneberg. You’ll have to try their homemade pasta plates and burrata and prosciutto appetizer.
  • Pequod’sCome here for deep dish pizza. This is by FAR my favorite. Deep dish pizza can be too dense and heavy for me. Pequod’s reuses their cast iron pans and adds cheese to their cornmeal crust so that it is crispy and flavorful. I once ordered a pizza with 13 toppings and Pequod’s managed to make it not soggy. 
  • Chicago Pizza and Oven Grinder – Their potpie-style pizza and Mediterranean bread are amazing. The pizza arrives and is flipped at your table so that the pizza in the bowl lands on the crust. It’s wild! Their salads are also great. It’s a cash only establishment and reservations are highly recommended. They’re booked out for weeks at a time. Watch our Instagram Reel to see what the food looks like.
  • Pizzeria Uno – Known for creating the deep dish pizza back in 1943. They have a tasty and chunky red sauce that makes the pie. We love their sausage too. Not into deep dish pizza? They also make thinner tavern-style pizza that will satisfy your taste buds.
  • Portillo’s – Come here for a legit Chicagoan hot dog. I had my first Portillo’s in Buena Park, California, and had to try the original in Chi-town! We highly recommend the jumbo Portillo’s dog with all the fixings, their Italian beef sandwiches “wet,” and pasta dishes!
  • Pizzeria Portofino – Another good spot to dine along the river
  • River Roast – A good American restaurant to dine along the river and take in amazing views of the Chicago skyline.
  • Rubi’s Tacos – Located in the Pilsen neighborhood on 18th Street, this Netflix-famous taco spot serves tacos and quesadillas on handmade tortillas. We also got to try their Barbie corn which was surprisingly delicious despite the neon pink color. Pilsen is known for delicious Mexican fare that can be found throughout 18th Street. 


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banh cuon rice wraps from Le Colonial in Chicago, Illinois

Banh Cuon from Le Colonia

Als Italian Beef Sandwich Chicago Illinois

Al’s Italian Beef Sandwich

What to Drink in Chicago

  • The Aviary – Even though the bubbling, foaming, crackling drinks here are quite expensive, you’re paying for an elevated experience in Chicago’s West Loop. They have drink tasting menus as well as a cocktail plus food pairing menu. It’s a great way to test out the Alinea group prior to booking a $1,400 dinner for two. Dress up for a night to remember. All reservations are made prior and paid for online.
  • Bar Avec – Craft Cocktail bar with great city views from the 8th floor. Reservations are recommended.
  • Cindy’s Rooftop for drinks and because it overlooks the Bean.
  • Dorian’s – Check out this speakeasy that is accessed through a record shop. They have DJs that play LoFi hits using vinyl records.
  • Dovetail Brewery – Local craft brewery with daily tours.
  • Estelle’s Café and Lounge: Estelle’s has been around for two decades. People love the art deco atmosphere, craft beer, and burgers.
  • Fox Bar – This snug hangout, located on the second floor of Soho House Chicago, is like drinking in your Dad’s basement. Play a record, order a pizza from a vintage payphone, and drink a cocktail in an upholstered chair with rolled arms.
  • The Game Room – Is part of the Chicago Athletic Association and offers craft cocktails and bar food in a posh setting. You can play games throughout the venue. The venue is also perfect for large groups! At the roof of the same building is Cindy’s Rooftop.
  • Goose IslandA once hyper-local craft brewery that is super popular and unfortunately owned by InBev. Still worth a visit to their Fulton taproom where you can purchase and taste their Bourbon County Stout (BCS) on draft.
  • Half Acre
  • The Highline Bar
  • Hopleaf Bar – Craft beers are all the rage at this Andersonville neighborhood staple, where no children are allowed. Choose from 68 draft beers and order food from the well-crafted menu.  
  • King of Cups – Immediately transport into the medieval times when you step into this dimly lit bar with creative craft cocktails.
  • Lagunitas Brewing Company
  • Love Street – Super swanky cocktail bar located in the neighborhood of Wrightwood and Wayne. They also offer dealer’s choice cocktails.
  • Monk’s Pub – Come here for delicious craft beer in a true pub style setting. Their Italian Beef anything here is great too. We highly recommend their Italian Beef poutine!
  • Mother Hubbards – This is THE PLACE to go to during St. Paddy’s day festivities. It’s conveniently located next to a bunch of other bars on Hubbard Street so you can easily bar hop. 
  • Old Town Ale House: This is a classic Chicagoan dive bar, full of misfits and great people watching. It’s one that Anthony Bourdain favored and included in his show.
  • Three Dots and a Dash – Awesome Tiki-inspired bar. Just be aware that the drinks are a little spendy!
  • RAISED – A rooftop bar with craft cocktails that are Instagram worthy! The bar is located on the third floor of the Renaissance Chicago Downtown Hotel.
  • Revolution Brewing
  • Scofflaw – Gin-centric masterpieces are served in this dark and dreamy nook-filled bar.
  • Sportsman’s Club – Do you favor manly rustic bars with copious amounts of taxidermy? This cash-only Ukrainian Village hangout has a funky backyard patio, perfect for late-night drinking.
  • The Violet Hour: Take a trip down the rabbit hole in trendy Wicker Park. Be sure to order an expertly crafted cocktail from the James Beard Award-winning beverage program.
Goose Island Halia Craft Sour Peach Beer

Goose Island Halia Sour Peach Beer

Chicago Travel Guide Map

Ready to explore Chicago? Use our travel guide map to keep track of the attractions, restaurants, and bars you want to see.

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