A trip to the windy city was long overdue in my travel diary and when we got the extended weekend during the 4th of July, we booked our tickets right away! Chicago – the third largest city in the US has all the hustle and bustle of a big city, with a Midwest charm. The Tall skyscrapers, incredible architecture and history, unique restaurants with amazing food options, world-class museums and urban gardens and parks – Chicago is one of the few cities in the world that has it all and beacons you to visit.
After spending the most amazing 10 day vacation in the city and I wanted to put together a travel guide that summarizes the top things to do in Chicago! Honestly there is so much to do, see, and eat in this beautiful city that it’s impossible to see it all in 2 -3 days in Chicago – but you can definitely see all the highlights that make the city so great. So I have structured this blog post to feature must-visit attractions and best dining options, so that you can mix and match things according to the number of days you plan to visit the city.
Hopefully, this post will make it easier to plan your next trip to Chicago!
A few things to know before you go:
When to visit?
The best time to vacation in Chicago is the summer, during the months of May through August. Summer in Chicago is like no other – the weather is the perfect mid 70s with cool wind blowing all through the day. It’s the ideal weather to travel around the city and explore, indulge in rooftop brunches or catch a pastel sunset against the city’s skyline.
Do you need a car?
Most Certainly No! Depending on where you stay, you can walk up to most of the places/attractions or take the train. If you stay anywhere on the Magnificent Mile, you can walk for most of the boat tours, restaurants, bars, attractions(Chicago Bean & Riverwalk) and Navy Pier. To other places like the museums, Grant Park and downtown restaurants – you can haul an Uber or take the L – line train.
What to pack?
When you visit Chicago during summers, you can pack a bag full of dresses, shorts and fun summer clothes but here are a few things you should add to your bag first:
- A pair of sneakers/comfortable shoes (you will be walking a lot)
- Umbrella (the windy city rains are unpredictable)
- Change for the train rides
- Cell phone chargers and cell phones – most of the places require digital passes or online reservation.
- Sunnies and a hat ( you need these to beat the heat)
Now to the main details:
Here’s an interactive map of the entire Chicago itinerary.
- Green – Places to stay
- Blue – Places to visit and see
- Yellow – Breakfast and Coffee spots
- Orange – Places to eat – Lunch and Dinner
- Pink – Places to grab a drink – Rooftop Restaurants and Bars
Where to stay
There are two main options to stay in the city, which is close to all the attractions and restaurants: Magnificent Mile area and Downtown Chicago.
The Magnificent Mile has tons of luxury hotels to choose from, but here are our top 2 picks:
Located in the heart of Magnificent Mile, Loews Chicago is a perfect blend of luxury and convenience. As soon as you walk in, you are swooped into a luxurious experience with a stylish lobby, a buzzing lounge, state-of-art fitness center with a pool and wonderful hospitality.
The rooms are equipped with modern appliances – a coffee maker, telephones with voicemail and wireless capabilities, a large flat-screen tv, professional hair dryer and a spacious work desk with an ergonomic chair. The Highlight of the room is the floor to ceiling windows showcasing some of the best views of the city ,Navy Pier and Lake Michigan. We could even catch a glimpse of the Navy Pier’s fireworks from our room.
Watch a quick Hotel Tour Here.
The hotel has a stylish rooftop bar(Streeterville Social), featuring delicious American eats & cocktails and is a cool spot to hang out at!
And Here’s the best reason to book your stay today – The hotel has an taken up an initiative to support local community and help the teachers and students as they prepare to head back into the classroom and operate in this “new normal. For any two-night (or more) stays booked from Memorial Day to Labor Day, Loews Chicago Hotel and Loews Chicago O’Hare Hotel will donate to DonorsChoose (an online non profit) to help fund Chicagoland school projects for the 2021-2022 school year.
Overlooking the Chicago River, this amazing hotel located in a high rise building is the perfect place to stay close to all the action of the Magnificent Mile. LondonHouse Chicago offers modern chic rooms with full amenities and have floor to ceiling windows overlooking the river and city. Don’t forget to check out the lobby bar and rooftop restaurant with some of the best views of the river.
In the Downtown Chicago Area we recommend staying at The Blackstone Chicago
The Blackstone is a name you don’t want to forget when planning your next trip to Chicago. Not only is it located in the heart of the Chicago loop area, but it’s where LUXURY meets epic history and contemporary attitude.
Housed in a 1910 beaux arts building across the street from Grant Park, this ornate hotel is within walking distance to the Field Museum, Shedd Aquarium , Museum Campus and Willis Tower – couldn’t get any better than that! The place also has a hip and colorful, boutique hotel vibe with a modern Spanish restaurant and a coffee shop on site!
Watch the Hotel and Room Tour Here!
Our Room was tastefully designed with artful amenities and had the best views of Grant Park, Lake Michigan and the Museum Campus.
Where & What to Eat
There are tons of amazing places to eat in Chicago! But here’s an important tip – make reservations at least 2 weeks beforehand! Many of these places fill up extremely fast, making it near impossible to get reservations. Here are a few of my fave picks in the city to try:
The newest French brasserie in the Carbon Carbide building, is a great spot for some delicious croissant, sandwiches and coffee to start your day. And the decor, is completely Instagram worthy.
Craving some savory crepes? Visit the Crepe Shop for some great sweet and savory crepe options with a full coffee bar. This place has a rustic vibe with high top seating and plant murals; Super Cute!
Hit this spot for some unique old fashioned donuts – real moist and dense. You ought to try their handcrafted donuts if you ever visit Chicago. Mocha Old Fashioned and Chocolate glazed donuts were definitely my favorites.
Calling all the Nutella lovers, for the ultimate Nutella experience. This cafe offers a long menu of hazelnut spread; You’ll find crepes, croissants, waffles, pancakes, gelato and French toasts slattered with Nutella.
Get ready for a Bohemian escape with globetrotting food + cocktails and breathtaking views of the Chicago River. It’s a great place to enjoy a romantic lunch on the riverfront patio filled with pink daybeds, Moroccan lanterns and lush greenery.
Must try: Green Curry Meatballs Pozole and Pescado ala talla Drinks: Beatnik Bloody and Spiked Coconut
Located inside Restoration Hardware, this is a beautiful, courtyard dining experience under a glass atrium complete with fountain, olive trees and chandeliers. Brunch to an amazing menu of sandwiches and burgers + mimosas/bellinis. I can’t recommend this place enough.
This place is perfect for a high end Chinese dining experience on a terrace serving a detectable menu of dim sums and noddles.
Must try: Steamed pork dumpling Shanghai style, Roasted Duck Noodle Soup, Traditional Cantonese Chow Mein.
If you visit Chicago during the Spring-Summer time don’t forget to checkout the secret garden pop-up at the Hubbard Inn. Between the months of June-July the entire place is set up with thousands of colorful blooms, lush greenery and floral themes. And what makes it even better is their mouth watering brunch with spring themed cocktails. We were there on a Saturday and it was very BUSY , So don’t forget to get your tickets for the pop-up event in advance.
Tulum vibes in Chicago? I’ve got you. On a hot summer day, we walked to this place for lunch + drinks and as we entered through the door, it truly felt like a tropical oasis. Lush green decor, seagrass fixture lamps, tropical murals and wooden furniture just add to the whole ambiance of the place and makes it one of the gems of Chicago. Ah! those tacos and margs, never tasted anything better!
Must Try: Mango Aguachile, Chicken Al Pastor and Carne Asada Tacos Drinks: Tulum Mio and Picante
Amidst the bustling of the city’s noise, we found this beautiful French- Vietnamese Paradise – Le Colonial. It features a dining room, bar and lounge, private chef’s dining room and an all-season terrace, each space very tastefully decorated. We went in here for lunch and ordered the Cha Gio(Shrimp Spring Rolls), Sui Cao Chien(Chicken Dumplings) and Com Chien(Signature Fried Rice)- and everything was delicious.
New Place Alert!! This is a fairly new place in the area serving some unique Mediterranean food . And their location is unbeatable; the dining patio is literally by the Chicago River with the best views of downtown. I loved their “build your own bowl” concept, where you pick the base/salad, protein and toppings and they cook it and put it all together for one tasty bit of a meal.
DRINKS/ ROOFTOP RESTAURANTS
I’m here for the views. Seriously, the London House Rooftop has some of the best views of the Chicago River with all its bridges and tall skyscrapers. 3 levels of Rooftop dining gives you a plenty of opportunities to take in sweeping views of Chicago river and Magnificent Mile while sipping on cocktails and enjoying small bites. We went there two days in a row( as we were staying at the London House) and absolutely loved it. This is a popular spot, so it’s safe to make your reservations in advance.
Must try: Udon Noddle Stir Fry, Mezze plate and Chicken Skewer Drinks: Tropicana Club, French Martini
Another place with a view, but this view is completely different from that of London House. At Terrace 16, you get to experience some great views of the Navy Pier and Lake Michigan. When you gaze down the menu, this place might seem a little expensive, but the views are completely worth it. If not, I’m sure the drink menu will have your heart- they have drinks to the elements of Fire, Earth, Air and Water. Okay how cool is that?
Some of our favorites were: From The Ground Up, Tropical Rain, The Terrace Michelada and The Windy City
Close out your full day of traveling and exploring Chicago with drinks at one of the city’s most epic rooftop bars. The Roof on the Wit is a summer hotspot on the 27th floor of the Wit Hotel. The stunning design of the rooftop bar which turns into a buzzy nightclub by the dusk and sweeping views of Chicago skyline has my heart.
You can dine to the award winning Executive Chef, Nathan Sears’s, flavors from Spain and the surrounding spice-bearing regions – You’ve got to try their Neapolitan style Pizzas. It is beyond flavorful.
Must Try: Spicy Chicken Pizza Drinks: Pomegranate Mule and Blood Orange Sidecar
After a tired day of exploring, hit the Cerise Rooftop bar to enjoy a refreshing drink or savory snack in hand, as you gaze at the panoramic view of Chicago’s skyline from the top of Virgin Hotel. After 10pm, the bar quickly turns into a dance floor as the DJ spins some tunes.
Drinks to Try: Not-So-Old Fashioned and the Evening Sunshine
Couldn’t snag a reservation to Duck Duck Goat, or want something a little bit more casual and hip? By the same Chef ,Stephanie Izard – Cabra is a fun rooftop spot at the Huxton Hotel. It puts a unique spin to classic Peruvian dishes , like Aji de Gallina Empanadas with pecan herbed chimmi; Chicharron Del Puerco – pork shank with mint strawberry salad and Arroz Con Pollo- Fried chicken with tangy rice.
Cabra has the best ambiance in town with a buzzing bar, live green foliage all over the place, excellent city views and a serene rooftop pool to sit by and sip your drinks.
Must Try: Lamb Empanadas and Arroz Con Pollo Drinks: Warming up in Oaxaca and Alpaca My Bags
I had so many friends recommend Three Dots and Dash before my trip to Chicago, and it definitely did not disappoint! A Speakeasy bar with Tiki Drinks? What’s not to like. The entrance is sort of hidden in the alley way but as you open the door you are immediately teleported to a tropical paradise. Think 200+ rums & luau bikes in a retro Polynesian setting.
Okay now onto the cocktails – Well can I just say, some of the best Tiki Cocktails I’ve ever had!!! The cocktails are created using the freshest exotic fruits and spices, the finest rums and distilled spirits, and juices and elixirs that are cold-pressed and concocted in house and the names are just too catchy to ever forget. I tried the Down Periscope – blended cocktail over crushed ice served in a large oval cup adorned with tiki dolls, silky nitrogen gas and tropical fruit toppings. It was SOOOO GOOD!
Must try Drinks: Down Periscope, Shotstapus and Three Dots and a Dash
Another spot I’ve got my hots for! Streeterville Social is chic rooftop terrace serving up alfresco dining, libations, and a celebration of all things summer. They have the #WeDrinkPink going on all through summer, featuring specialty pricing on pink cocktails, rosé and food- which is a perfect opportunity drink up your favorite pink cocktails. For food we tried the Blistered Shishitos, Korean Sticky Wings and Mediterranean Chicken – and everything was so good. Its a great spot for brunch or early dinner to take in some mesmerizing views of the city as you sip on delicious cocktails.
Unique Cocktail Destination or Floral Paradise? I can’t pick a word. Located on the bustling Division Street, serving a globally-inspired, modern-American menu with an innovative craft cocktail program – this place has the most unique cocktails you would have ever tried. But the highlight of the place is an onsite flower shop – they let you pick your own flowers and create a bouquet which is then beautifully arranged and set up at your table while you dine. Okay this definitely made this one-of-a-kind dining experience in Chicago. (you’ve definitely got to try this place)
Must Try Drinks: Bonnie and Clyde, The Firebird, Caged and Infused and Kevin Bacon
If you’re a fan of Chinese food, you can’t miss Duck Duck Goat during your Chicago trip.
The main focus of the menu is house-made dumplings and hand pulled noodles They sound simple but they are so, so delicious — especially the XIAO LONG BAO. The duck & goat soup dumplings were perfectly steamed and were some of the best dumplings I’ve ever had.
Must Try: Peking Duck, Xiao Long Bao and Duck Fried Rice Drinks: Tropicoal and New Moon
The celeb chef behind Duck Duck Goat — Stephanie Izard— has two other restaurants in the area. Cabra is a rooftop Peruvian restaurant serving delicious tapas style food and you will need a reservation (weeks in advance). Little Goat Diner is in the Randolph Restaurant Row and houses the Sugargoat – a new bakery featuring a playful collection cakes, cookies, and cupcakes in unusual flavors including caramel corn, avocado toast and cheez-it.
Looking for a casual place with Asian bar eats and drinks – I know just the place. Bixi Beer is a trendy brewpub serving craft brews and cocktails and some yummy Asian inspired snacks. With a bright sun-soaked, plant filled atrium of dining room, craft bar and an outdoor patio offering scenic views of Logan Square , this place looks fabulous for an early dinner.
Must Try: Rangoon Royale, Spicy Fried Chicken Sando, Cumin Lamb Noodles and Japanese Cheescake
An Italian steak & pasta spot on 3 levels with a vast wine list, 2 fireplaces & a roof deck. If this isn’t inviting enough the food is just scrumptious. We got the Pappardelle and Spaghettini & Meatballs – both were loaded with all the goodness of flavor, cheese and meat. The highlight of their drink menu is the Manhattan which comes with GT symbol engraved ice cubes – by far the coolest drink I’ve sipped.
You can’t go to Chicago and not try the city’s most famous food item, the deep dish pizza. The question is – where? So here’s my favorite spot to get one of the fresh and cheesiest deep dish pizza – Giordano’s. They have multiple locations that are close to some popular attractions, such as Millennium Park, the Magnificent Mile, and Navy Pier, so it’s an excellent choice if you are pressed for time but want to get a pizza fix. Their specialty is the Chicago Classic Deep Dish, which has everything you need from a deep dish pizza – a crisp, flaky crust, fresh tomato sauce, plenty of cheese, and tons of toppings!
The Ultimate, most unique dining experience of Chicago – The Rose Garden at the Darling Chicago. Think hi-tea snacks and exotic cocktails amidst a rose garden in your own private glass greenhouse – Utterly romantic. We celebrated my Birthday here and I was head over heels in love with the whole vibe and experience of this place.
You can step inside to experience the swanky library and ballroom adorned with British manor-style decor. The Library offers pop-up performances from musicians, dancers and puppeteers (perched on a secret stage) while you dine. And for a long list of intricate cocktails and healthier food options, head upstairs to the Ballroom.
Seriously, do yourself a favor and get a reservation here during your trip in Chicago, you will thank me later.
Must Try: Short Rib Beignets with Peanut Dipping Sauce and Traditional Sausage Rolls Drinks: Desert Rose, The Darling Buds of May and Emerald City
Even though Chicago is famous for deep dish pizza, they have tons of pizza parlors serving Neapolitan-inspired pizzas prepared in wood-burning ovens. I personally prefer my pizza’s extra charred and roasted and I was in food coma when I tasted a slice at the Parlor Pizza Bar. Great Ball of Fire is my favorite – there are so many unique flavors you can try( with a mug of beer) and instantly fall in love with the flavors.
Things to do
The Windy city has so much to offer – from boat tours to museum tour, skyline views to “up in the clouds” experience. I’ve compiled a list of some of the best things we did and enjoyed, during our vacation.
Before you go Tip: Purchase the City Pass/ All-inclusive Pass from gocity.com if you are visiting for 3 days or more. Depending on the duration of your trip and the number the attractions you wish to cover, these passes will give you all-in-one access to 26 attractions at a great price. It’s a great way to explore all of Chicago with an easy digital pass which lets you mix and match your pre-booked activities.
One of the largest urban park in the Chicago Loop area; encompassing the Museum Campus, Buckingham Fountain and Millennium Park. Its a great place to set up a summer picnic, ride a bike or just stroll around and take in the expansive skyline views of the downtown. We went in during sunset and enjoyed a romantic stroll through the park while the sun set behind the tall skyscrapers and painted the sky pastel.
While exploring Grant Park, stop to admire the impressive Buckingham Fountain. Not only is the Buckingham Fountain one of Chicago’s most famous landmarks but it is also one of the largest fountains in the world! The fountain is an impressive 280 feet in diameter and has three basins with four Art Deco-style seahorses that represent each of the states that border Lake Michigan – Illinois, Indiana, Michigan, and Wisconsin. The size of the fountain is said to symbolize the enormity of the lake, and uses some 15,000 gallons of water per minute – super Impressive right?
At night, lights and music also accompany the display, and ends with a climax that shoots water over 150 feet in the air with a backdrop of the Chicago skyline! – It’s quite a show !!
If you didn’t go to the Bean, did you even go to Chicago? The iconic bean also known as Cloud Gate is a sculpture completely made out of stainless steel (which gives it that reflective property)! Created by Anish Kapoor a London based artist, the bean was unveiled in 2004 along with the park it sits in (Millennium Park). The sculpture was inspired by liquid mercury and on a clear day, you can see the reflection of the entire surrounding skyline and green space on the bean. It’s the most quintessential place to snap your first few photos in Chicago.
- Get in there early to avoid the crowds (preferably before 9am)
- After checking out the Bean, be sure to spend some time checking out the rest of what Millennium Park has to offer!
- Make sure you walk under the bean to see a cool visual effect
The Lurie Garden is a 3-acre botanical garden located in downtown Chicago’s Millennium Park. Visit this park for some of the best photos of Chicago.
Visit one of the largest aquarium in the world housing 32000 animals including the giant pacific octopus, sharks, Caribbean reef and belugas. The aquarium has some unique experiences like feeding the stingrays, meeting a penguin , 4D and virtual reality underwater tours. My favorite was touching the sturgeons (living fossil of the Great Lakes). Feeling their leathery texture and bony plates, was one a kind experience you’ll never forget. It’s a perfect attraction for families and kids.
From underwater experiences, now it’s time to move back into the past era and journey through the evolving planet. Yes I’m talking about the evolution of man from apes, ancient Egyptian and Tibetan civilization remains, various kinds of rocks and gems that comprises our earth and DINOSAURS. The Field museum is home to the largest T-Rex fossil ever found on earth – SUE and you get a chance to experience it’s world up close.
We enjoyed the Griffin Halls of Evolving Planet, where we saw many creatures that have roamed the earth throughout history, from single-celled organisms to our extended human family. The museum houses nearly 40 million artifacts and specimens, and trust me there is so much to see, you can make a day trip out of it.
Located in the Jackson Park, this is the largest science center in the Western Hemisphere. It has both an illustrious history and a focus on the future of science and education. We didn’t have much time to check out this museum, but I’ve heard its really great for children. The museum campus is also in full swing during the Cherry Blossoms season with about 160 cherry blossom trees. It’s utterly picturesque and definitely a must visit for photography enthusiasts.
Nestled in the urban jungle, Lincoln Park Zoo is dedicated to being the place in Chicago for all things wildlife. Home to almost 200 species – from lemurs to lizard and various flora and fauna – you can learn all about their habits and habitats. The admission to the zoo is free and hence do not require any reservations.
There is also a lush prairie-style garden filled with native plants and brimming with birds, frogs, fish and turtles in the zoo campus which is a wonderful way to connect with the natural world.
Okay here’s your chance to see the city from up top! Visit 360 Chicago, an observation deck on the 94th floor of the John Hancock Tower for some breathtaking panoramic city views. From here, you can get clear views of the Lake Michigan, skyline and 4 states(Michigan, Illinois, Wisconsin and Indiana). Thrill seekers may also choose to go on Tilt, a ride with an enclosed glass and steel platform that tilts outwards over 1000 feet above the Magnificent Mile, giving you a unique, downward facing window overlooking the city!
The Willis tower and Skydeck is a MUST DO while in Chicago. It’s the best way to get amazing views of the city while conquering fears by sitting on the glass floor! You will definitely feel like you’re on top of the world as you look out into the city and beyond from the 103rd floor of the Willis Tower, aka the second tallest building in the Western Hemisphere.
The highlight at Skydeck is the Ledge, a glass box that hangs out from the edge of the Willis Tower, giving you unparalleled views of the city – from 1353 feet above ground! It’s definitely the place to get some cool photos!
In my opinion, the best times to visit the Skydeck is early in the morning to beat the crowd and get some killer photos or during sunset to see the twinkling lights come alive against a dramatic sunset. But mind you, it does get pretty crowded during the sunset as it is the most popular time to visit the Skydeck. I would suggest getting the Chicago City Pass/All-Inclusive Pass, as this includes a day/night ticket, along with priority admission to lots of other attractions in the city – a great way to save money on your Chicago itinerary and also checkout the Skydeck during the day and sunset.
During your Chicago trip, spend some time walking along the Riverwalk, a 1.25 mile pedestrian trail along the south bank of the Chicago River spanning from Lake Shore Drive to Lake Street. Walking along the river may not sound exciting but it’s the perfect way to see the city!
Along the way you’ll find many restaurants, cafes and bars where you can stop by for a bite or a glass of wine. You can even rent a kayak from one of the docks there. You can choose to spend just 30 minutes here – or an entire afternoon! And oh did I mention that the Riverwalk has excellent photo ops of the skyline and river? You should definitely spend some time watching the boats go by, and admire all the bridges along the river and be sure to wait to see a bridge lift to let a boat pass through – one of the coolest sights on the Riverwalk!
A 1000m pier located on the Chicago shoreline, Navy Pier is a fun place to visit on a sunny day! Navy pier was built in 1916 has gone through some significant changes over the years. It’s currently home to a Ferris wheel, tons of shops, restaurants, a merry go round and more. It’s a fun place to walk down or hop on a skyline boat tour. You can also get great views of the city!
Ready to shop till you drop? This is the commercial district in Chicago where all the best shopping is. The North Michigan Avenue is lined with hundreds of retailers – from giant shopping malls, popular department stores, luxury designer stores, and trendy boutiques –It’s definitely a shopaholic’s paradise!
It’s also a great city walk with some amazing restaurants and tourist spots along the way.
That beautiful river flowing through the city amidst all the skyscrapers and a magnificent lake with breathtaking views bestows a lot of boat tour options and here are some of my faves:
Chicago is a city known for its architecture, and the best way to take it in is to see it from a boat while cruising down the river!
In the aftermath of the Great Chicago Fire, with hundreds of thousands of people left homeless, the city had to rebuild and a lot of effort was placed on architecture. From constructing a city with wood, they shifted to constructing steel-frame buildings, leading to the development of some of the first modern skyscrapers in the world. The end result is today, Chicago has a totally unique skyline.
Most tours start from Navy Pier or Michigan Avenue and take about 75 minutes. With a fully narrated tour, you will learn a lot about the architectural styles of the buildings and the history of Chicago. There are also plenty of photo opportunities, so don’t forget your camera for the most Instagrammable shots of the Chicago skyline!
You can do all this while you sit back and relax with a beverage in hand. Is this the best way to explore the city or what? This was definitely the highlight of our trip to Chicago and would definitely recommend as a must-do activity.
If you want a different perspective of the Chicago skyline and see the building lights twinkle against the night sky, you may also want to consider a night tour, which are available from mid-May until mid-October.
If you got the All-inclusive Pass, the Skyline Lake Tour is another option you should do to get some best views of the skyline. You typically hop on the boat at the Navy-Pier and cruise along the the coastlines of Lake Michigan and enjoy some stunning views of the Chicago Downtown.
You don’t want to miss the Chicago skyline at night, and it’s even better with an up-close view of the Navy Pier fireworks! All through the summer, every Wednesday and Saturday night, Navy Pier lights up the Chicago skyline with a wonderful display of fireworks and you can hop on a boat to get to see the fireworks from beyond the shoreline. It was truly the most mesmerizing experience of them all and we absolutely loved it.
Thank you for reading and hope this helps you plan your next trip to Chicago!
3 Day Itinerary
Here is the ultimate take away from this blog post – a fun filled 3 Day itinerary of Chicago!! This itinerary contains all the must-visit highlights of Chicago and some of amazing restaurants in the city, you definitely need to try. Hope this itinerary helps you experience the best of the windy city and fall in love with it!