Welcome to Chicago: the Windy City-that architectural wonder, Great Hall of iconic foods, and vibrating culture, all mushed in one. From busy streets to tranquil parks in Chicago, I’m now going to take you on a perfect three-day itinerary, right from the dizzying heights of Skydeck Chicago to the rewarding depth of a Giordano’s deep-dish pizza. Join me in the core exploration of this incredible city.
Day 1: Symbols of the City
Morning: Have a sumptuous Breakfast
A day in Chicago starts in one of the favorite locals, Goddess and the Baker. This seats conveniently opposite Millenium Park and opens at 7:00 AM in the morning, thus meeting expectations of that kind of people that get up very early in the morning. Have a different taste of breakfast from different kinds of omelets at 12$ to yogurt parfaits at a meager 9$. Of course, never miss their signature Rainbow Cake; it’s a colorful treat blowing up with hues and sweetness. A slice goes for $7, a good catch for two reasons: to start off your morning.
Mid-Morning: Millennium Park and The Bean
After breakfast, it takes only a few minutes to reach Millennium Park, the architectural jewel in Chicago’s crown. Though 24.5 acres big, this is not a quantity-over-quality park but rather filled with artistic and cultural amazements. Head toward the iconic Cloud Gate, better known as ‘The Bean,’ designed by Anish Kapoor. This is ideal for photo shoots, reflecting skyscrapers of the city with its 110-ton elliptical mass composed of 168 plates of stainless steel.
Head slightly off center in the park to find the Lurie Garden: a 2.5-acre botanical oasis of tranquility in the middle of the city. Then there is the Crown Fountain: an interactive water feature that’s at least worth your attention during warmer parts of the year.
Insider’s Tip: If you’re here in summer, be sure to catch a performance at Jay Pritzker Pavilion. This innovative outdoor concert venue regularly hosts free music events; check local listings for events during your visit.
Afternoon: Cultural fest at the Art Institute of Chicago
A few minutes from Millennium Park, the Art Institute of Chicago is one of the oldest and biggest art museums in the country. To be more precise, it houses more than 300,000 pieces of works within its collection. Entrance is approximately around $25, though it is money well spent so that you can see some of its well-renowned exhibits such as “Of Gods and Glamour” to the contemporary “Landscape in Light.”.
Big museum, allow at least 3 hours here if possible. Open from 11 AM-5 PM, so that would probably be the best place to go right after lunch.
Insider Tip: It is here that the museum’s miniatures room is found-a must-see of intricately crafted historical interiors from the world over.
Evening: Dazzling Views and Dining at Navy Pier
Conclude your first day at Navy Pier, a 3,300-foot-long pier on the shores of Lake Michigan. This Chicago landmark offers more than just scenic views; it’s a hub of entertainment with rides, theaters, and eateries. Around sunset, take a spin on the Centennial Wheel. Tickets are $18 for adults, providing stunning panoramic views of the city and lake.
Dinner options are galore on this pier, with over 30 restaurants available for dinner. One highly recommended place to try dinner includes Giordano’s Navy Pier, where you can get famous deep-dish pizza as low as $20. You will have classic Chicago-style pizza for dinner here-a great way to wrap up the day.
Sunset at Milton Lee Olive Park
After dinner, if you’re up for a bit more exploration, walk north to Milton Lee Olive Park. It’s a quieter area known for its spectacular sunset views over Lake Michigan. The park’s serene atmosphere and picturesque fountains make it an ideal spot for reflection after a bustling day.
Day 2 – Open Viewed Places
Morning: Energy-Releasing Breakfast Options
Begin your second day in Chicago with an energetic breakfast. Choose between the following two restaurants, both of which are located near your next destination, the Magnificent Mile:
1. Wildberry Pancakes & Café – Renowned for their pancake menu, the Wildberry blissfully opens their signature Berry Bliss Pancakes starting at $15. Furthermore, it contains an extended breakfast menu with the variety of omelets, French toast, and different specialty coffees that range between $10 and $20. Cozy atmosphere and good service-just what one would want for an early start.
2. Beatrix: If you’re looking for lighter, healthier fare, Beatrix is your healthiest option. Specialty foods fresh and wholesome, run from avocado toast for $12 to quinoa cakes with poached eggs for $14. A freshly squeezed juice bar-accompaniment to your meal, if desired-includes such energizers as green juice at $8.
Insider’s Tip: Lines can get a little crazy at Wildberry-especially on weekends. Get there early, or be prepared for a short wait-it’s worth it!
Mid-Morning: Coffee Like No Other
After having breakfast, make a visit to the Starbucks Reserve Roastery. A few blocks from where one can find the locations for breakfast, this is not just any ordinary Starbucks. Five-storeyed, 35,000 square feet, this happens to be the largest Starbucks in the world. It is much more of an experience rather than a cup of coffee, from its rare, small-lot coffees brewed by different methods.
Prices for special brews begin at about $10, while special pastries can run from $5 to $8.
Insider Tip: Don’t miss the Roastery exclusives, like Whiskey Barrel-Aged Cold Brew. Take your drink up to the rooftop for one of those real Chicago moments.
Late Morning: Take a Walk Down the Magnificent Mile
Next, take a casual walk down the most famous commercial district in Chicago: the Magnificent Mile. This stretch houses shopping-with over 400 stores from boutiques to the most posh designer stores. Even if the purpose is not to shop, the architecture alone-from historical churches and structures to modern skyscrapers-is something worth seeing.
Lunch and Afternoon: Marks of Genius in Architecture and Leisurely Promenades
Lunch will be on the Magnificent Mile. One could dine with the myriad restaurants available from Shake Shack’s affordable grub-as meal deals start at about $10 to 15-to The Purple Pig’s sit-down meals that begin at approximately $20.
Afternoon: Head down to the nearby Chicago Riverwalk. So much more than a pretty 1.25-mile pathway along the Chicago River, you can take in public art installations and plush gardens, popping into a riverside café to get your caffeine fix with a quick pick-me-up. There are also architectural tours on the waterfront by boat; $40 gets a ticket for a guided tour of iconic skyscrapers and historical buildings comprising Chicago.
Insider’s Tip
Don’t miss an awesome view of the setting sun over the Chicago skyline with a twilight cruise.
Evening: Cultural Shows at Chicago Theater
Spend your evening at the historic Chicago Theatre. Recognized for its magnanimity and catering to nothing but the best in terms of entertainment, it counts amongst the most renowned places to enjoy a live show or even stand-up comedy. Take a guided tour in the theatre for approximately $20 and get to know about its rich history and architectural values.
Dinner: Deep-Dish Delight
For dinner, if you liked dinner the first night, you will head out for more classic Chicago deep dish at Giordano’s. You can fill up here for about 25 bucks a head, but this is one of those classic things to have in Chicago.
Day 3: Major attractions and Cultural hotspots
Daytime: Spectacular Panoramic Views: Skydeck Chicago
Begin your last day with a visit to Skydeck Chicago, located within the Willis Tower, which was the tallest building in the world, at one time. Get there early; the doors open at 9AM. It would cost $30 each, but the views of the city from the 103rd floor are spectacular, and on a clear day, one can behold a view of as many as four states and a distance of over 50 miles.
For the more daring, there’s nothing quite like stepping out onto the Ledge—a glass box extending four feet outside the building—unique, though vertiginous, city views.
Insider Tip: Purchasing the tickets online and in advance saves queuing time. You’ll also get the chance, through this early visit, to have ample daylight when viewing the city from up high and even the golden hour in the morning.
Mid-Morning: Take a Coffee Break at Mojo Coffee
Coming down from the dizzying height of Willis Tower, head toward Mojo Coffee. A block away, Mojo was born in New Zealand-the reason for its trendy quality. Have the famous flat white for approximately $4, or coupled with a baked good that costs about $5. This is a stylish café for contemplation after your visit and for planning the day.
Late Morning: Grant Park Walk and Buckingham Fountain
From here, head to the “front yard” of Chicago, the 319-acre Grant Park. With its impressive sculptures, gorgeous parks, and the popular Buckingham Fountain, the latter is one of the largest fountains in the world. Besides an hourly display of spectacle waters, it transforms each night into color and music in a magical display of light and music.
These shows are free to watch; therefore, this will be an excellent economic activity.
Lunch: Al Fresco Dining near the Park
For lunch, make reservations at one of the restaurants surrounding Grant Park. The Gage offers contemporary American dining in its dining room and outdoors on its patio where stunning park views and Michigan Avenue people-watching complement your meal. Entrees begin at 20 dollars.
Afternoon: Museum Campus Deep Dive
Spend the afternoon on the Museum Campus. A 57-acre park, some of the premier museums the city is known for include:
• Field Museum: Home to Sue, the largest T. rex fossil ever found. Adult admission is $26 and grants access to everything from the tombs of ancient Egypt to the halls containing dinosaurs.
• Shedd Aquarium: Among the largest indoor aquariums in the world, this contains over 32,000 different aquatic animals. Entry will cost about $40 for adults in order to get special exhibits like the Caribbean Reef.
• Adler Planetarium: Enjoy learning with the space-based shows and exhibitions, partly free, although entrance to all of the overall exhibitions and experiences costs about $35.
Insider’s Tip: If you think you might go to more than one of these, be sure to check out a Chicago CityPASS for $108 – a real steal that will save you real money plus gives you some very nice VIP access.
Evening: North Avenue Beach – Relax at this beach in Chicago as the day comes to a close and enjoy stunning views of a Lake Michigan evening sunset. You’ll take a guided tour through an extremely unique beach house built into an ocean liner design with upper decks offering great skyline views. Dinner For dinner head down the beach to Castaways Bar & Grill for a casual dinner quite literally on the beach. Try one of their famous fish tacos or have a Chicago-style hot dog for $15 per person. This a great place to reflect on your visit and take in the breeze off the lake.
Conclusion
You will only scratch the surface with three days in Chicago, but this itinerary does ensure that the best this amazing city has to offer is seen-from the towering skyscrapers to a delicious taste of deep-dish pizza. Be it masterpieces hanging in museums or casual walks through its vast park systems, every nook and corner of the city will narrate its saga. Have a great trip to Chicago, and remember: there is always something left to come back for.
