The Ultimate Chicago Travel Guide

Looking for the ultimate guide to Chicago? You came to the right spot. Chicago is one of the major U.S. cities that you absolutely have to visit at some point in your life. In some ways, it’s similar to New York City — the energy is electrifying, the food is fantastic, and the city is very walkable. But, in other ways, Chicago is a city that is completely unmatched. You can’t go wrong with a vacation to Chi-Town, but when it comes to the best things to do, where to eat, and where to stay, check out all my Chicago travel recommendations below!

How to Get to Chicago

flying into chicago

Before we can jump into the Chicago travel guide, we have to get you there! If you live close enough, you can always drive and park in the city or at your hotel. Otherwise, you can take the Amtrak to Union Station, or hop on a plane to one of Chicago’s two airports, Midway or O’Haire International Airport. In my opinion, O’Hare is much easier to navigate, but it all depends on where you are coming from. 

The Best Way to Get Around in Chicago


Similar to New York City, Chicago is known for being very walkable. If you are staying somewhere near The Loop or River North, you will definitely be able to walk to nearly all of the main attractions. If you are staying up north near Lincoln Park, Old Town, or Gold Coast, walking may be a little bit more difficult.

Chicago Public Transportation

If you are up for the challenge and feel comfortable navigating the public transportation system, download the Ventra app and grab a card at any kiosk to gain access to all of the terminals. 

Taxis, Ubers, and Lyfts

Taxis are fairly inexpensive in the city, and many times, they are safer than the public transportation system (especially at night). 

The Best Time of Year to Visit Chicago

Unless you love slugging through the snow in negative temperatures and bone-chilling wind, you should visit Chicago during the warmer months (April through October, although the month I’d most recommend is August!). Personally, I only like snow when it’s accompanied by a luxury ski resort and Aprés, but to each their own! If you love St. Patrick’s Day, you could also try to plan your trip around the holiday so that you can see the famous green river.

Where to Stay in Chicago

LondonHouse Chicago


Part of Hilton’s Curio Collection, LondonHouse Chicago has it all: the perfect location on the river, state-of-the-art amenities, and the best rooftop bar in the city (more on this later!). This hotel is perfect for a romantic getaway, but could also be great for a solo trip or a weekend with the girls. If you stay here, be sure to order their chocolate chip cookies via room service and enjoy them in your plush LondonHouse robe! 

Waldorf Astoria Chicago

Photo courtesy of

Nestled in the luxurious Gold Coast neighborhood, the Waldorf Astoria Chicago is the perfect location for travelers who want to escape the hustle and bustle of downtown Chicago. Just a six-minute walk from the beach and a five-minute walk from Magnificent Mile, this pet-friendly luxury hotel has everything you need and more!

Four Seasons Chicago

Photo courtesy of Four Seasons

We all know I’m a Four Seasons junky, so of course I had to include Four Seasons Chicago! Four Seasons hotels are known for their luxurious spas, gorgeous rooms, and top-notch customer service, but they are also one of the best there is when it comes to family accommodations! Four Seasons Chicago has childcare services, a kids club, and cribs available for patrons traveling with infants.

Viceroy Chicago

Photo courtesy of the New York Times

Another hotel nestled in the Gold Coast neighborhood is Viceroy Chicago. Viceroy has a beautiful rooftop pool and lounge with sweeping views of the city, and some of the best luxury shopping is just a short walk away!

Peninsula Chicago

Photo courtesy of

If you read my guide on where to stay in New York City, then you saw that Peninsula New York was one of my top recommendations. So, it makes sense that I love Peninsula Chicago! This hotel features a full-service Asian-inspired spa, award-winning restaurants (yes, there is more than one!!), and is a stone’s throw away from all of the action as it is located right on Magnificent Mile.

The Ritz-Carlton Chicago

Photo courtesy of Ritz-Carlton

The Ritz is a household name, and for good reason. No one does accessible luxury quite like the Ritz-Carlton does! And their Chicago location is no exception. The Ritz-Carlton Chicago has a stunning spa, dry cleaning services, and a tasty restaurant to boot!

The Langham Chicago

Photo courtesy of Conde Nast Traveler

The Langham Chicago features warm, neutral tones with dark wood in every room, making their guests feel welcome and at home. If you are looking to relax, be sure to visit their award-winning spa for a massage, facial, or other treatment. Or, just soak in your giant tub overlooking the city with a glass of cold champagne!

Where to Eat in Chicago

Chicago has some of the U.S.’s best dining experiences, many of which are award-winning favorites! Just remember, you have to make reservations in a city like Chicago. Otherwise, you’ll miss out on some really great food!

Maple & Ash

Photo courtesy of Wine Mag

If you are looking for a luxurious, unforgettable dining experience in Chicago, make a reservation at Maple & Ash! Although the menu is quite pricey, you probably won’t get a better meal in the city in terms of both food and ambiance.

Albion Manor

Photo courtesy of Chicago Star Media

As of this year, Albion Manor is Chicago’s hottest English-style pub! The upstairs cocktail bar is to die for, so even if you only grab a drink here, be sure to check it out. 


Photo courtesy of Kasama

Kasama is a Michelin-star-rated restaurant located northwest of downtown Chicago. This modern Filipino restaurant is a must-see while in the city!


Photo courtesy of Chicago Eater

Located in Chicago’s Gold Coast neighborhood, Alpana focuses on wine-inspired cuisine that is served in a relaxed, intimate atmosphere (my kind of place!!). The owner, Alpana Singh, is a nationally-acclaimed Sommelier who works with her team to create dishes designed to complement wine from all of her favorite producers around the world!


Photo courtesy of Tabu

This eclectic spot in the West Loop should be your go-to if you love Latin cuisine and fresh cocktails! Plus, the artistic flair is totally Insta-worthy.

Billy Goat Tavern

Billy Goat Tavern is one of the oldest and most historic restaurants in all of Chicago. The original location is located underground near the riverwalk, which is a fun experience in itself! When you go, be sure to order a double cheeseburger to stay so that you can sit and enjoy the old-school dive bar atmosphere. 


If you are looking for a killer Chinese restaurant with a Michelin star, look no further than MCCB! Grab a bite to eat here while you are exploring Chinatown (be sure to get their dumplings as an appetizer — they are to die for!!).


Photo courtesy of Food Detective

Craving some Italian cuisine and culture? Head to Monteverde in the West Loop! Monteverde is great for both lunch and dinner (the outdoor patio section is so cozy in the warmer months!).

Little Goat Diner

Photo courtesy of Boka Restaurant Group

Little Goat Diner is another West Loop favorite that features contemporary takes on American classics! Come here for breakfast and order pancakes or the shrimp and grits. Soooo yummy!


Photo courtesy of The Infatuation

Ema serves Mediterranean and Middle Eastern cuisine that will have you feeling like you are halfway across the world! They are well known for their kabobs and tapas, so be sure to try some when you go.

Smith & Wollensky

Photo courtesy of Smith & Wollensky

Everyone needs to visit a solid steakhouse when visiting the Midwest, and if you’re in Chicago, Smith & Wollensky is the place to go! Although the menu items can be slightly pricey, the view of the river is SO worth it.

The Best Deep Dish Pizza in Chicago

I can’t talk about Chicago without talking about deep dish pizza! Chicago is known for their deep dish pizza joints, but out of all of the options, which should you try? These four are my go-to’s!

Gino’s East

Gino’s East has two locations in Chicago (one near Magnificent Mile and one just south of The Loop). Other than its pizza, Gino’s is well known for its walls which are covered in signatures from past visitors! When you go, be sure to ask for a pen to leave your mark.  

Lou Malnati’s

I’m going to say it… Lou Malnati’s is my favorite deep dish pizza place in all of Chicago! This may be a hot take (you can ask literally anyone on the street what their favorite is, and everyone will tell you somewhere different), but it truly is so good. Be sure to put in a reservation, though, because the wait time is usually crazy long!


Photo courtesy of Giordano’s

Giordano’s has three locations in the city, so you should be able to find one close to you no matter where you are. 

Pizzeria Uno

Photo courtesy of Trip Advisor

Pizzeria Uno is where Chicago deep dish pizza was created, so it’s a must-see when you’re in the city (even if you only see it from the outside)!

The Best Bars in Chicago

Whether you are looking for a refreshing daytime drink or a fabulous cocktail to kick off an evening out on the town, Chicago has an incredible bar scene that you can’t miss! But, just like the restaurants in Chicago, reservations are usually required (you’ll thank yourself later!).

The Signature Room Lounge

Looking for a breathtaking view of the city with a glass of crisp white wine in hand? Head up to the 95th floor of the John Hancock building to The Signature Room Lounge! The Signature Room also features a restaurant on the 96th floor, but in my humble opinion, there are many other restaurants that are way better, so I recommend just grabbing a drink here. 

Shore Club

Photo courtesy of Event Up

Listen up ladies — if you are visiting Chicago on a girls’ trip or for a bachelorette party, Shore Club is a can’t-miss spot!!! Rent a cabana and bask in the Chicago sun with your girls as you look out onto the ocean-like Lake Michigan. It’s like being at the beach… but in the Midwest! If you can swing it, bottle service here is so much fun!

Nine Bar

Photo courtesy of Secret Chicago

If you find yourself in Chinatown and want to grab a drink, head over to Nine Bar for a yummy cocktail or sake! I highly recommend their Mai Tais.

Mother’s Ruin

Photo courtesy of The Infatuation

Many New York bars and restaurants end up with a second location in Chicago, and Mother’s Ruin is one of them! Mother’s Ruin was originally founded in NYC in 2011, and its success in The Big Apple led them to open up in The Windy City shortly after. Here, you can expect exceptional cocktails, a great beer list, and some of the best mezcal negroni in the city!

Rose Lounge

Adalina’s Rose Lounge is a swanky speakeasy with dark decor and some seriously sexy cocktails! This is definitely a hidden gem in Chicago, so it won’t be as crowded as some of the other places on this list.

Bar Mar

Chicago might be 12 hours away from the nearest ocean, but that doesn’t mean that they don’t have incredible seafood and nautically-themed cocktails! When you go to Bar Mar, order their oysters or lobster rolls with your drink. 

The Best Rooftop Bars in Chicago

If you are going to pay for a cocktail in Chicago (because let’s face it, they aren’t cheap!!), you may as well get a stunning view to go with it. Here are the best rooftop bars in Chicago that you have to see when you visit! 


Photo courtesy of Raised

This hip rooftop bar is located in the heart of downtown Chicago. They are open year-round, but rooftop bars are always better in the warmer months!


Looking for a view of Millenium Park and The Bean? Try Cindy’s Rooftop!

Chateau Carbide

Photo courtesy of Chateau Carbide

Located atop the Pendry Hotel is Chateau Carbide. As the name suggests, this rooftop lounge is nothing short of luxurious! Come for the champagne and city views, but stay for the swanky seating and DJ on Friday and Saturday nights.

LH Rooftop

If you end up staying at LondonHouse Chicago, LH Rooftop will be your go-to spot! Guests of the hotel can go to the rooftop at any time without a reservation, but even if you aren’t staying here, LH Rooftop is the #1 rooftop bar that I would recommend visiting in Chicago. The views are unmatched!

What to Do in Chicago

There are countless things to do in Chicago, and you probably wouldn’t be able to hit them all even if you lived here for a decade. But while you are visiting, you should try to at least experience a handful of these attractions!

Walk Around Wrigleyville and go to a Cubs Game

Whether or not you are a Cubs fan, Wrigleyville is a super fun area to explore! If you have the time, catch a Cubs game for the true Chicago experience. 

Second City Comedy Show

One of the must-sees of Chicago is definitely Second City! Many of the most famous comedians of our time got their start at Second City, some of the most notable being Tina Fey, Stephen Colbert, Steve Carrell, and of course, the late Chris Farley. There are tons of shows running all week long, but if you can stay up a little later, catch one of their last shows of the day! For some reason, they are always better IMO.

Take an Architecture River and Lake Cruise

If you do ONE THING in Chicago, let it be this! An architecture tour on the river and lake is the absolute best way to experience the city. There is so much history packed into Chicago, and this tour helps you learn all about it in just a couple of hours!

Explore the Riverwalk

A visit to Chicago wouldn’t be complete without a walk along the river. No matter where you start to walk, there are tons of art exhibits, cute cafes, and some of the best people-watching in the Midwest!

Walk Through Gold Coast

Whenever I visit Chicago, I always take a morning to walk through the gorgeous and historic Gold Coast neighborhood with a cup of coffee. Some of the city’s nicest townhomes and most spectacular mansions are located here, so if you decide to explore, here are the main sites I would hit:

  • The Cardinal’s Mansion (1526 N Astor Street)
  • The McCormick Mansion (20 E Burton Place) 
  • The Original Playboy Mansion (1340 N State Parkway)
  • Wooden Alley (half a block south of Lincoln Park between N State Parkway and N Astor Street)

Shop on Michigan Avenue

There are countless shops on and around Michigan Avenue, some of my favorites being Water Tower Place, The Shops at North Bridge, and of course, Saks Fifth Avenue!

Visit the Starbucks Reserve Roastery

I know, I know… Starbucks can be so basic. But the Starbucks Reserve Roastery in Chicago is their largest location in the entire world, so it’s worth walking into while you’re there!! If you are a Starbucks connoisseur, you have to grab a cup of joe here (and maybe a souvenir!).

Walk Along North Avenue Beach

Photo courtesy of

You may need a bit of exercise after all of the yummy food you will eat in Chicago, so take a walk (or jog) along North Avenue Beach and soak in the views!

Take a Photo at The Bean

Did you even go to Chicago if you didn’t take the obligatory photo at The Bean (AKA Cloudgate)? The Bean is an art exhibit that was created specifically as a tourist attraction. That artist must be pretty proud because it’s definitely at the top of most tourists’ lists (although, admittedly, it’s kind of anti-climactic). 

Explore Navy Pier

Another major tourist attraction is Navy Pier. If you aren’t into crowds and major tourist traps, you could probably skip this one (and The Bean). But if you’re visiting Chicago for the first time, it’s probably worth experiencing at least once! Navy Pier features a ferris wheel, a beer garden, and some of the best gelato in the city (IMHO). If you are lucky, you might even catch some live music here!

Have a Picnic in Grant Park

If time allows, grab a blanket, some food to go, and a bottle of wine to share with your friends or significant other in Grant Park! Renting a bike to ride around the park is also super fun, and while you are exploring, don’t forget to snap a photo of Buckingham Fountain (it’s truly immaculate!).

Take a Photo in Front of The Chicago Theatre

Photo courtesy of The Chicago Theatre

The Chicago Theatre is a breathtaking masterpiece that is absolutely iconic. Even if you aren’t able to catch a show inside, snap an Insta-worthy photo in front of the giant marquee!

Visit Skydeck at Willis Tower (Formerly Known as Sears Tower)

Photo courtesy of Get Your Guide

By this time, you have probably gotten a pretty good view of the city from bars, restaurants, and the river cruise. But if the Chicago skyline is still in your sights, stop by the Skydeck at Willis Tower (formerly and better known as Sears Tower) for some killer views!

Walk Through Lincoln Park’s Honeycomb Boardwalk

The Nature Boardwalk at Lincoln Park Zoo, better known by locals as Honeycomb Boardwalk, is an Insta-worthy spot in Chicago! This boardwalk is gorgeous year-round and is the perfect backdrop for a romantic stroll.


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