A midwestern girl born and raised, who better to offer an in-depth Chicago itinerary for those who are planning a trip to Chicago? A gorgeous city situated along the coast of sprawling Lake Michigan, there are endless things to do in the Windy City! From Navy Pier to Millennium Park, visitors to Chicago are sure to fall in love.
This Chicago itinerary will make planning a trip to Chicago easier than ever. I’ll include sections on top things to do in Chicago, how to get around in Chicago, where to stay in Chicago, best Chicago tours, where to eat in Chicago, and more!
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Chicago Map
Ready to book your trip to Chicago? Check out Skyscanner to find the best deals on flights from your departure city and take the first step towards an unforgettable midwest vacation!
Top Things to Do in Chicago
Navy Pier
If you’re a tourist in Chicago, you’re required to visit Navy Pier. Take a ride on the massive ferris wheel to enjoy breathtaking views over Lake Michigan and the entire city. One of the best things to do with kids in Chicago, the entire family will love the shops, restaurants, gardens, and theaters at Navy Pier. Among the most visited tourist destinations in the Midwest, Navy Pier should definitely be the first stop on your Chicago itinerary!
My pick for best Navy Pier tour: Signature Food Tour at Chicago’s Navy Pier
Millennium Park
When you think “Chicago”, Millennium Park is probably the first thing that comes to mind. The iconic Bean statue and other of the city’s famous sculptures can be explored here, and Maggie Daley Park offers a variety of seasonal activities all year long. Go ice skating in winter, watch free concerts and movies in the park in summer, and bring your kids to the lively Crown Fountain.
My picks for best Millennium Park tours: Chicago’s Greatest Hits Bicycle Tour; Big Bus Chicago Hop-On Hop-Off Tour; Chicago in a Day: Food, History and Architecture Combo Tour
Chicago Food Tours
One of the country’s best foodie cities, you should definitely sign up for a Chicago food tour while you’re in the city! From filling deep-dish pizza to classic Chicago hot dogs, there’s truly no better way to experience authentic Chicago culture than through its food!
My picks for best Chicago Food tours: Chicago Favorites Ultimate Food & Walking Tour; Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour; Underground Donut Tour: Chicago’s First Donut Tour; Chicago Pizza Tour
FREE Lincoln Park Zoo
The Lincoln Park Zoo is great for a Chicago family vacation. Situated in a peaceful neighborhood filled with parks and not far from the lake, the zoo is a fun activity for all ages and best of all, it’s completely free! Not only is the zoo one of the best fall activities in Chicago, but in the winter, you can add ZooLights to your Chicago itinerary, too!
My picks for best Lincoln Park Zoo tour: Go Chicago Pass: Save Up to 55% on Top Attractions
Exploring Chicago Neighborhoods
One of the best parts of Chicago is exploring the city’s charming neighborhoods! Each with its own distinct character, you’ll want to spend time experiencing all that these areas have to offer. Pop into a Second City show in Old Town, check out a Cubs game in Wrigleyville, and search for Wicker Park’s quirky hidden gems. Either rent a divvy bike and ride through the city or sign up for a Chicago neighborhood tour and explore the best of Lincoln Park, Old Town, Lakeview, River north, the Loop, Boystown, Wrigleyville, Wicker Park, Bucktown, and more!
My picks for best Chicago neighborhood tours: Gangsters and Ghosts Tour in Chicago; Chicago Neighborhoods Tours ; Bike Tour of Chicago’s Lakefront Neighborhoods
Chicago Museums
Home to some of the best museums in the country, you’ll definitely want to add a few museums to your Chicago itinerary! Don’t miss out on The Field Museum, the Shedd Aquarium, the Museum of Science and Industry, The Adler Planetarium, The Art Institute of Chicago, and more.
My picks for best Chicago museum tours: Chicago CityPASS; Must-See Museums in Chicago
Chicago Architecture River Cruise
Take a breathtaking Chicago River Architecture Tour and cruise down the river to admire the city’s world-renowned architecture. Discover the rich history of Chicago as told by its fascinating cityscape. Your guide will offer a unique look into the history of Chicago’s city planning and details about its magnificent skyscrapers and most iconic buildings. Chicago architecture tours are a favorite amongst Chicago visitors and locals alike.
My picks for best Chicago Architecture tours: Chicago Architecture Tours; Chicago Architecture River Cruise
Chicago Lakefront
Situated on the shores of Lake Michigan, Chicago’s lakefront is the crowned jewel of the city. Head to North Avenue Beach to soak up the sun and go for a swim, ride bikes along the Lakefront Trail, have a picnic by the water, or take a scenic walk with views of the stunning Chicago skyline. You can’t miss a visit to the lake when planning a Chicago trip!
My picks for best Chicago Lakefront tours: Private Boat Rental with Navy Pier Fireworks and Pizza Included; Chicago Lakefront and Museum Campus Small-Group Segway Tour; Chicago Lakefront Segway Tour
The Magnificent Mile
Head to Michigan Avenue for a mile of upscale shopping, hotels, restaurants, and more. The Magnificent Mile cuts through the heart of Chicago’s downtown and is the city’s primary commercial and shopping district. Here you can visit Water Tower Place shopping mall, ride up to the 360 Chicago Observation Deck at the John Hancock Center, check out a show at the nearby Theatre District, or take a stroll along the gorgeous Riverwalk.
My picks for best Magnificent Mile tours: The Magnificent Mile Tours; 360 Chicago Observation Deck Admission: Skip the Ticket Desk; Chicago Crime and Mob Tour
Chicago Nightlife
No visit to Chicago would be complete without checking out the city’s vibrant nightlife! Every neighborhood has something different to offer, from dive bars to high-end nightclubs. Whether you’re in the mood for a patio, rooftop bar, pub, live music concert, speakeasy, karaoke bar, or anything else, Chicago has got you covered!
My picks for best Chicago nightlife tours: Top Nightlife Experiences in Chicago; Spirit of Chicago Sunset Dinner Cruise with Buffet; Skip the Line: Tommy Gun’s Garage Dinner and Show Ticket
Chicago Sports
Chicago sports are the beating heart of the city and Chicago fans are some of the best. Depending on the season, head to the Windy City to watch the Cubs, Bears, Blackhawks, Bulls, White Sox, and more. If tickets to the game aren’t available, head to any sports bar in the city to get the authentic Chicago experience all the same!
Best Chicago Tours
No Chicago itinerary is complete without some great Chicago tours! When you’re planning a trip to Chicago consider adding some of these classic tours:
Chicago Architecture Boat Tours
360 Chicago Observation Deck Skip the Line Tours
Go Chicago All-Inclusive Pass – Save up to 55% on Top Attractions
Where to Stay in Chicago
My picks for where to stay in Chicago: Hyatt Place Chicago/Downtown – The Loop; Chicago Getaway Hostel; Kinzie Hotel
You have lots of great options for where to stay in Chicago. When planning a Chicago trip, it’s important to think about what you’ll be doing. If you’re looking to hit the hottest tourist spots in the heart of all the action, you should consider staying in downtown Chicago, either in River North or the Loop. If you’re looking for a super luxurious stay, Gold Coast hotels might be more your style.
If your Chicago itinerary calls for a more authentic, neighborhood vibe, you’ll want to stay farther north, in the Lincoln Park, Old Town, Lakeview, or Wrigleyville neighborhoods. If you’ve been to Chicago a million times and are looking to get a bit off the beaten path or if you’re on a budget, consider staying on the up-and-coming West side in Wicker Park, Bucktown, or Logan Square. Note that Lake Michigan is east of the city, so the further east you go, the closer to the lake you’ll be, and therefore the more expensive your accommodation is likely to be as well.
How to Get Around in Chicago
When planning a Chicago trip, you’ll want to get a good handle on how to get around in the city. Luckily, Chicago is an incredibly easy city to navigate and you’ve got lots of options for Chicago public transportation. Chicago’s CTA system includes busses and trains which will get you pretty much anywhere you would need to go in the city. Consider buying a Ventra card online or at any of the “L” stations and adding money as necessary, or if you plan to stay longer, consider buying a monthly pass.
The city is very walkable, though depending on your Chicago itinerary you might consider using shared city bikes, which in Chicago are Divvy bikes. Uber, Lyft, and UberPool (Pool option not available during the pandemic) are typically available and are affordable ways to get around the city as well.
Where to Eat in Chicago
There are SO many options for where to eat in Chicago, the list is absolutely endless! From classic Chicago-style dishes to some of the world’s finest cuisine, Chicago is a food lover’s paradise. Here are a few of my favorite bars and restaurants in the city to add to your Chicago itinerary!
My Favorite Bars in Chicago
London House rooftop bar – The Loop
Blind Barber– West Loop
The Vig – Old Town
Benchmark – Old Town
The Violet Hour speakeasy – Wicker Park
Gaslight Bar and Grille – Lincoln Park
Old Crow– Wrigleyville & River North
The Original Mother’s – River North
My Favorite Restaurants in Chicago
RPM Italian – River North
Etta – Wicker Park & River North
Aba – West Loop
Cafe Babareeba – Lincoln Park
Time Out Market – West Loop
North Pond – Lincoln Park
Tango Sur (BYOB!!) – Wrigleyville
Dry Hop – Lakeview
The Girl and The Goat – West Loop
Sweet Mandy B’s – Lincoln Park & Streeterville
Best Spots for Deep Dish Pizza and Classic Chicago foods
Lou Malnati’s– Deep-dish pizza
Giordano’s– Deep-dish pizza
Garrett Popcorn– Caramel corn and cheese corn
The Wiener’s Circle– Chicago-style hot dog
Portillo’s – Chicago-style hot dog and Italian Beef
Gibsons Bar and Steakhouse – Steak
Check out my Recommended Travel Essentials page for more useful resources for planning a trip to Chicago!
Chicago Tips and FAQs
When is the best time to visit Chicago?
Hands down the best time to visit Chicago is during the summer. The weather is warm and the city is alive after a long, cold winter. That said, fall in Chicago is beautiful and the weather is pleasant, and same with spring. Though winter in Chicago can be bitter cold, activities like ice skating, the Christkindlmarkt, hot chocolate, and the TBOX winter bar crawl make visiting Chicago in the winter worth it! If you’re planning a Chicago trip, you can’t go wrong visiting any time of year, but you’ll find the most things to do there during summer.
Is Chicago safe?
For the most part, yes, Chicago is safe. Though Chicago has an international reputation for crime and unrest, those areas are isolated from the main tourist and downtown areas. Serious crime exists in pockets of the city’s South Side and West Side, but visitors to Chicago will likely stay around the downtown Loop areas and the neighborhoods just north of that, which have little to no reported crime.
What foods is Chicago known for?
Chicago is definitely known as a foodie city, and for good reason! Classic Chicago staples include deep-dish pizza, Chicago hot dogs, Italian beef sandwiches, Garrett popcorn, and Chicago steaks.
What are the airports in Chicago?
Chicago has two main airports, both serving international destinations. They are Chicago O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW).
Traveling Alone or Want to Join a Tour?
If planning a Chicago trip is overwhelming and you’d rather hop on an organized tour which includes a knowledgeable local guide, consider checking out Intrepid US Tours for your Midwest travels! Intrepid Travel offers guests a true authentic experience and really does a great job of connecting you with locals and giving you a flavor for the local culture and vibe. Affordable and sustainable travel-focused, Intrepid Travel is my favorite tour company for my own travels and I can’t recommend them enough!
*Please note that some of the above are affiliate links. At no additional cost to you, I make a small commission if you choose to make a purchase. Please know that I ONLY recommend products that I personally use or believe to be helpful to other travelers!