Chicago, Illinois is an incredible city with so much to offer. It has Midwest vibes with big-city dining options, attractions, and shopping. And then there are the stunning Lake Michigan views and Chicago Riverwalk to boot. Chicago is a great city for a quick weekend visit, with plenty to see and do, and endless delicious food and drink possibilities.
In this Ultimate Chicago City Guide, we are excited to share everything you need to know to make the most out of your trip to the Windy City, including the best things to do, neighborhoods to stay in, restaurants to eat at, and more!
Top Ten Things to Do in Chicago
Narrowing it down to ten things to do in Chicago is a difficult task. There are so many wonderful things to see, neighborhoods to explore, museums to visit, and “must-do” activities that this list will really only skim the surface. That being said, here are my favorite tried and true Chicago recommendations for those visiting the city.
1) Try Chicago’s Famous Deep-Dish Pizza
No trip to the Windy City is complete without a visit to either Lou Malnati’s, Giordano’s, or Gino’s East. Better yet, try all three and decide for yourself who really makes the best deep dish pizza in Chicago!
There will likely be a wait at any of these famous Chicago institutions – either go at an “off” time, around 3-4 pm, or put your name down and grab a drink at a nearby bar. If you’re not interested in trying the deep dish, these restaurants offer thin crust pizza as well – the best is at Lou Malnati’s.
2) Check Out The Lincoln Park Zoo
The Lincoln Park Zoo is a free zoo in the middle of the city. In addition to seeing giraffes, elephants, and rhinos right in the heart of Chicago, you will get killer views of the Chicago skyline from the Nature Boardwalk.
Once you are done exploring the zoo, wander a few minutes north to soak in the beauty of Lincoln Park.
3) Take An Architecture Boat Tour Along The Chicago River
Everyone loves the infamous Chicago architecture boat tour, and for good reason. The buildings that you will see are beautiful, and you will learn all about the interesting history of Chicago!
The boat tours last 1-2 hours and are a great, unique way to see the city from the water.
4) Soak In The City Views, Either From The Hancock Tower Or The Willis Tower
You’ll have to buy tickets and wait in line to get to the top of the Willis Tower, but if you’ve ever wanted to step out onto the Sky Deck (a glass enclosure 1,350+ feet in the air), you will have to get a ticket.
To avoid the lines while still soaking in similar views, make a reservation at the Signature Room on the 95th Floor of the Hancock Tower. Same views, but no ticket required! You will be required to order one menu item per person in your party, but this is usually less expensive than the cost of the Observation Deck ticket, and you will not have to wait in line.
Either way, be sure to head to the top of one of these two towers and relax while you soak in the 360-degree views.
5) Check Out An Improv Or Sketch Comedy Show At Second City In Old Town
This is where Steve Carell, Tina Fey, and so many other incredible comedians got their start. Be sure to reserve tickets in advance. Second City is certainly a Chicago “must-see” and will not disappoint.
6) Go For A Stroll Along Lake Michigan
Start at Navy Pier (feel free to ride the Ferris wheel, if that’s your thing) and head south along the lakefront. You will see Grant Park to the right, and beautiful Lake Michigan to the left.
7) Visit Millennium Park And Take Photos In Front Of Cloud Gate (Also Known As The Bean)
Wander through Maggie Daley Park to the North Rose Garden, and through Grant Park. While you are in the area, head over to Cindy’s Rooftop Bar in the Chicago Athletic Association around sunset and enjoy the views.
There is usually a fairly long line to get to Cindy’s Rooftop, but it moves quickly. You can make reservations in advance — if you are able to do so, you will avoid the line!
8) Go To The Beach. In Downtown Chicago
Yes, really. Pack up your towels and sunblock and spend an afternoon relaxing on Oak Street Beach or North Avenue Beach.
At Oak Street Beach, you can rent beach chairs, and enjoy food and drinks at Oak Street Beach Cafe. There are also bike rentals and volleyball rentals available.
North Avenue Beach offers similar amenities, in addition to yoga, watersport rentals, kayak rentals, luxury beach chairs, and beach umbrellas.
9) Do Some Shopping Along The Magnificent Mile
With everything from Neiman Marcus and Cartier to Zara, Nike, and Sephora, there is something for everyone along North Michigan Avenue.
If you need a sweet treat while shopping, head to Do-Rite Donuts. And if you need lunch along the way, Purple Pig is a few blocks north of the river and is an excellent tapas restaurant.
While you’re in the area, explore the quaint side streets between North Michigan Avenue and Rush Street.
10) Kayak Along The Chicago River
Weather permitting, kayaking the river is an excellent way to see the city. Alternatively, take the water taxi to China Town and you’ll get to the same great views.
How To Get Around In Chicago
Chicago is an extremely walkable city. If you are feeling really ambitious, you can walk from Lincoln Park to Old Town, swing through the Gold Coast neighborhood, down the Magnificent Mile, through River North, across the river and down to the Loop. Most of the recommendations in this city guide are within walking distance of one another.
You can ride the L (Chicago’s rapid transit train system). You can use the official Chicago Public Transportation Website to plan your trip, see fares, and check if there are any disruptions.
Otherwise, Uber and Lyft are widely available.
Neighborhoods And Where To Stay In Chicago
River North is the neighborhood just above the Chicago River. Hotels in this area are within walking distance of the Chicago Riverwalk, the Magnificent Mile, and countless excellent dining options.
If you would like to stay right on the Riverwalk, try the Langham Hotel or the Westin Chicago Riverwalk Hotel. A few blocks north of the river, there is the Gwen Hotel, in addition to several various Marriott and Hilton hotel options.
If you are going to Chicago primarily to hit the shops and enjoy some great meals, the Magnificient Mile is the place to be. There are some luxurious hotels along North Michigan Avenue, many of which offer Lake Michigan views.
The Loop neighborhood is the closest to all of the museums. It is also within walking distance of fabulous lakefront real estate, which is convenient if you are looking to run, bike or walk along the lakefront while you are in town.
If you would like to stay in the Loop area, consider the Chicago Athletic Association Hotel (be sure to check out the game room on the second floor, as well as Cindy’s Rooftop Bar), LondonHouse Chicago, or the J.W. Marriott Hotel.
Where to Eat in Chicago
There is SO much good food in this city that it is hard to decide where to eat if you have limited time in town. Have fun eating your way through the city.
There are also a surprising number of bars with incredible views. The best place to check out the views indoors is the Signature Room at the Hancock tower, so keep this in mind if the weather isn’t 75 and sunny when you are in town!
Best Modern Italian Food In The City: Monteverde, West Loop
Dinner at Monteverde is perfect for a celebration, special occasion, or just plain old dinner out. The restaurant is beautiful and the food is outstanding.
Make a reservation as far in advance as possible. And if you do go for a celebration, let your server know and they will serve a noteworthy slice of cake for dessert.
Perfect For Tacos And Margs: Big Star Taco, Wicker Park
Any time its patio weather in Chicago (which translates to: sunny and above 55 degrees…) Big Star is a great choice. The Wicker Park location opens at 11 am on weekends, and I would recommend showing up around a quarter to 11 to get in line.
Enjoy the tacos, patio margarita drinking, and people watching. And if you are there on the later side, I recommend you head right across the street to the Violet Hour.
Best Steak In Town: Bavette’s, River North
Don’t be surprised by wait times between two and three hours! Just put your name down and head to Gilt Bar, Mercadito, Celeste, or Three Dots and a Dash for a beverage while you wait.
You can opt to sit in the bar lounge, which tends to have a shorter wait. The food is definitely worth the wait – the steaks are all outstanding, as is the burger, and you cannot go wrong with any of the side dishes.
Bavette’s is BYOB – the house rule is that your server will waive the corking fee if you send a glass of wine to another patron in the restaurant. You might even get lucky and be on the receiving end of the bargain!
Mediterranean Food In A Trendy Setting: Ema, River North
Ema is another restaurant where every menu item is delicious. If you like hummus and babaghanouj (“charred eggplant” on the menu) spreads and the food that usually follows, you will love Ema.
Go for the seasonal risotto and the beef tenderloin kebabs. This is one of my all-time favorite meals.
Vegetable-Focused, All-Around Outstanding Food: Bad Hunter, West Loop
The West Loop is home to most of the new, trendy, restaurants with nearly-impossible-to-get reservations. Bad Hunter is one of the best.
Vegan-friendly with plenty on the menu for everyone in your party. The cocktails are noteworthy, as is any burrata dish on the menu.
The Unofficial Best Hamburger In The World: Au Cheval, West Loop
The double cheeseburger with bacon AND a fried egg at Au Cheval has been named the best burger in the world. No Chicago city guide would be complete without mentioning it.
There will be a lengthy wait to try this burger for yourself, but just put your name down and head across the street to grab a cocktail at Girl and the Goat while you wait. Or wander up and down West Randolph street to check out the other trendy restaurants in the West Loop – maybe you’ll get lucky with a last-minute cancellation!
After dinner, head to Jeni’s for ice cream, if you have room.
Best Bars in Chicago
Chicest Speakeasy In Town: The Violet Hour, Wicker Park
My personal favorite speakeasy in the city is The Violet Hour. This place is seriously chic, with delicious craft cocktails, good music, and good vibes.
The entrance is just a door painted into a large mural, directly across the street from Big Star Taco in Wicker Park. There is a little black gate just to the right of the door, which should help you locate it.
There may be a short line (which will be a dead giveaway for the speakeasy entrance), but it moves fairly quickly and the cocktails more than make up for the wait.
Best Views Of Chicago: LondonHouse, River North
This hotel bar is worth a visit any time the weather is nice – bring a sweater because it is outdoors and up quite a few stories! LondonHouse offers excellent views in all directions – of the Chicago River and surrounding buildings. It is pretty much guaranteed that anyone visiting Chicago will be awestruck by the views.
Best For People Watching: City Winery, River North
This outdoor bar is located right on the Chicago Riverwalk. Literally the first day the sun comes out in Chicago (might be March… might be May…), this place is packed. And it seems to stay that way until it is just too cold to spend any time outdoors anymore.
It is easy to spend a whole afternoon watching the boats, people, and dogs go by while enjoying a cold beverage (yes, they have beer and cocktails as well!).
This speakeasy-ish bar has consistently excellent bartenders, excellent cocktails, and a very chill, old-school Chicago vibe. You can tell the bartender your liquor of choice and the general taste you are looking for in your cocktail, and be surprised by the deliciousness that is served. Moneygun is one of my favorite places to grab a drink before or after dinner in the West Loop.
General Tips And Advice For Visiting Chicago
When To Visit
Visit in the summer or fall. It’s Chicago, so that’s a given, right? Everyone knows that Chicago is cold, but not everyone realizes exactly how long the cold lasts.
It can be pretty chilly in April and even into May. The months from June through, and including, September is a fairly safe bet, weather-wise. Be sure to pack for all seasons – you may experience winter, spring, summer, AND fall in the same trip.
What To Do During A Rainy Day
If it winds up being cold, rainy, or both while you are visiting, there is still plenty to see and do.
You can visit the museums or enjoy the shops along the Magnificent Mile. You can take an architecture boat tour (even in the rain!) or sit back and enjoy the views from the Signature Room on the 95th floor of the Hancock Tower.
My favorite activity on a chilly winter day in Chicago is to laugh the cold off at a comedy show at Second City.
What To Do During A Sunny Day
If the weather is nice, spend a whole morning or afternoon sipping coffee or wine on the Chicago Riverwalk. There are several Adirondack chairs set up right where the River Walk begins, just after Lake Street and below West Wacker Drive. This is a great place to sit and people watch, enjoy a coffee while you read a book, soak in the sun or watch the boats and kayakers go by.
The architecture boat tour really is as fantastic as everyone says it is. It is worth the money and a few hours of your visit. If at all possible, go when the weather is good and you will have a great afternoon. There is a bar onboard the boat.
When summer starts in Chicago, everyone is out on Lake Michigan. If you are there when the weather is nice, grab a few friends and rent a boat for a few hours. Lake Michigan is truly beautiful and it is a treat to see the city from the water.
Chicago City Guide Wrap Up
Chicago is one of the best cities in the world. From great food, to countless unique bars, to beautiful architecture and museums, you won’t run out of things to do in the Windy City.
I hope this guide helped you plan your trip to the city!
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