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The spires of hundreds of steel-framed skyscrapers make the iconic Chicago skyline instantly recognizable. Set against the sweeping backdrop of Lake Michigan, the U.S.’s third largest city is where natural beauty meets manmade marvels.
From lakefront parks to sky high observation decks, wherever you view Chicago from, your eyes will be given no reprieve. With museums aplenty, a world-class food scene and a fascinating history, Illinois’S mammoth metropolis rivals even New York on the U.S. city break front.
Chicago is perfect for a weekend getaway; our 3 day Chicago itinerary packs in as much as possible. But, no matter how long you have to spare, make sure the Windy City is on your U.S. bucket list. One day will allow you to check off Chicago’s most famous sights. Adding a couple of extra nights to this 3 day Chicago itinerary would give you the opportunity to explore nearby Milwaukee or head to Springfield, Illinois’ sleepy capital, and pay tribute to Abraham Lincoln.
And if you’ve got just one day in the windy city, here is the guide you need.
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When to visit Chicago
With mild summers and cold winters, the best time for this 3 day Chicago itinerary boils down to personal choice. All the main attractions are open year-round and there’s plenty to do inside when the weather isn’t on side.
Summer is perfect for cruising Lake Michigan, whereas winter brings beautiful snowy scenes and a warm festive atmosphere. Hotel prices tend to be lower away from major holidays. Though, as in all big cities, they fluctuate greatly depending on what’s-on.
Getting to Chicago
By air
Served by two major airports, Chicago is one of the easiest U.S. cities to reach. Chicago O’Hare International Airport (ORD) is the city’s main hub. With connections from across the globe, including daily flights from several European cities and the Middle East, if you’re visiting from overseas, the chances are this is where you’ll arrive.
From the airport, the CTA Blue Line takes just 45-minutes to Downtown with trains running 24-hours per day.
Chicago Midway Airport (MDW) is served mainly by low-cost carriers. A major hub for Southwest, there are frequent services to cities across the United States as well as destinations in Canada and Mexico. CTA’s Orange Line connects Midway with Downtown in around 30-minutes. Find the best options for your travel plans by comparing flights before booking.
By land
As the Mid West’s largest transport hub, Chicago is well served by intercity train and bus services. Amtrak operate several daily services from cities around Illinois along with neighboring Michigan and Wisconsin. Long-distance trains connect Chicago with destinations as far afield as New York, Seattle, New Orleans, San Francisco and Los Angeles. Intercity buses provide frequent and cost-effective connections across the Mid West including Detroit, Milwaukee and Minneapolis.
Getting around Chicago
Travelers visiting from Europe or Asia will know only too well that U.S. cities often don’t have the best public transport options. Chicago, however, has a surprisingly comprehensive transit network. Even if you’ve rented a car, or brought one with you, getting around Chicago is easy by public transport.
The Chicago Transit Authority (CTA) provide bus, train and metro services throughout the city and suburbs. Tickets are affordable and contactless cards are accepted on buses and at stations. To save on travel costs for this 3 day Chicago itinerary, a 3-Day CTA pass will cover all your journeys within the city. Of course, taxis are readily available to hail on the street and rideshare apps like Lyft and Uber are on hand 24/7.
Where to stay for your 3 Day Chicago Itinerary
The thing about three day trips is that they sound like a long time, but are always over in a flash. Especially in Chicago where there’s so much to see and do. To get the most from this 3 day Chicago itinerary, choose a hotel in Downtown. The Loop and Near North Side (which includes the iconic Magnificent Mile) are our top recommendations.
The Loop
Covering the area of Downtown south of the Chicago River, The Loop is home to some of Chicago’s finest museums, tallest skyscrapers and best theaters. Our number one choice here is the London House Hotel. Dating back to 1923, the building was once home to the London Guarantee and Accident Company.
Beautifully repurposed in 2013, London House is now one of Chicago’s leading luxury boutiques. Aside from lavishly decorated rooms and a serene spa, the hotel boasts a gorgeous rooftop bar and two high-end restaurants.
A long time Loop favorite, River Hotel offers the ultimate balance of value and comfort. Right on the riverfront, overlooking the Wrigley Building and the towering Trump International Hotel, the River Hotel features a gym and complimentary breakfast. It’s well worth paying a small premium for a room with river views.
Slightly further south of the river, Arlo Chicago is a fantastic choice for those who seek out modern simplicity. In the heart of Chicago’s theater and museum district, Arlo is ideally positioned for sightseeing during this 3 day Chicago itinerary. On top of swish modern rooms, expect a free breakfast daily and a lively bar with regular live sets.
Near North Side
Home to wonderous Magnificent Mile, Chicago’s finest fashion boutiques and world-famous Lake Shore Drive, Near North is the ultimate base for first timers to the Windy City. Our top pick, just two blocks from North Michigan Avenue (Magnificent Mile) is ACME Hotel Company. With a modern industrial-chic style, highlights include a craft cocktail bar and on-site bakery.
If you want to stay right on the Magnificent Mile, the Warwick Allerton Chicago is our top pick. Whilst part of a (small) chain, it certainly delivers on the boutique feel. A hotel for almost a century, it offers the perfect blend of history and modern comforts. The recently renovated rooms stand in wonderful contrast with the elegant Lobby Lounge, an ode to the glamour of yesteryear.
A summer favorite, The Wade is the place to stay if you want to be by the lakeshore. Overlooking Navy Pier, with stunning views across Lake Michigan, The Wade is luxurious without a luxury hotel price tag. An indoor pool, trendy restaurant and cosy bar are the highlights; whatever you do, splurge on a lake view room.
3 Day Chicago Itinerary
Day 1: All Things Magnificent
Morning: Arrive and settle in
No matter what time you arrive to kick off your 3 day Chicago itinerary, head to your hotel and offload your bags. There’s plenty of walking to be done today and that’s never fun with a suitcase in tow.
Admittedly a bit touristy, but a great way to get your bearings in a new city, kick off your visit with an open-top bus tour. You’ll pass many of the locations included in this 3 day Chicago itinerary with the added benefit of an audio guide to learn a little about the Windy City’s long and rich history.
Afternoon: The Magnificent Mile
The Magnificent Mile is to Chicago what Times Square is to New York. We’ve all heard of it, and skipping it would simply feel wrong. Start your first afternoon in Chicago at 360 Chicago towards the Mile’s northern end. Our top Chicago observation deck, catapult yourself 94 stories above North Michigan Avenue to enjoy a sweeping panorama of the entire city. Book in advance to skip the line when you arrive.
Back on solid ground, walk south down North Michigan Avenue pausing at the historic water tower and window shopping as you work your way south towards the Chicago River. The Magnificent Mile is home to Chicago’s finest luxury boutiques. From Burberry to Bloomingdale’s, if you’re on the hunt for designer clothes or stylish jewellery, Magnificent Mile is the place for you.
If, however, you’re anything like me and the prices make your eyes water, you can always take refuge in the world’s biggest Starbucks.
Late Afternoon: The Chicago River
At the southern tip of the Mile, pause by Du Sable Bridge to take in one of the finest views of the Chicago skyline. The Wrigley Building, built between 1920 and 1924 for the Wrigley confectionary company (who are still Chicago-based, but no longer occupy the building) is partially open to the public and well worth a look. If you’re traveling with younger children, The Museum of Ice Cream directly opposite will likely be a far bigger draw.
Next, head to the pier at the foot of the Wrigley Building to join an architecture cruise along the Chicago River. This fully guided hour-and-a-half boat trip (45-minute option also available) showcases some of the Windy City’s most iconic architecture. You’ll pass beneath the Willis Tower, Chicago’s tallest building, and learn about the birth of the steel-framed skyscrapers for which the city is so famed.
Evening: Chicago’s Most Famous Dish
There can be no more appropriate way to round of day one of this 3 day Chicago itinerary than by sampling the city’s most famous food: Deep Dish Pizza.
Created by Rudy Malnati, a pizza chef at Pizzeria Uno, Deep Dish is baked in a thick pan, notable for its buttery crust and having the cheese placed underneath the tomato sauce. Rudy’s son Lou went on to found his own pizzeria, now famous for their version of Chicago Deep Dish.
A little like the battle of the cheesesteaks between Gino’s and Pat’s in Philadelphia, both claim to serve the best, and original, Deep Dish. Now, Pizzeria Uno and Lou Malnati’s have several locations around Chicago (and further afield) and the general consensus is, they’re both as good as each other. Of course, the only true way to find out is to try them both and with three days in Chicago, there’s always time for a second pizza.
Day 2: The City on the Lake
Morning: Art & Beaches
Made famous by Aliotta Haynes Jerimah’s 1971-song, Lake Shore Drive (or LSD as it was known long before the other meaning of the acronym came about) is one of the most photographed spots in Chicago. Busy no matter the time of day, LSD is the kind of place you don’t mind getting stuck in traffic; the views of Lake Michigan are phenomenal.
Start day two of this 3 day Chicago itinerary at Oak Street Beach. Created purely by accident when a shipping pier was built in the late-19th century, Oak Street Beach was once rife with crime. Now a tad safer, this is the place to go for the most impressive view of the city skyline.
Head south along Lake Shore Drive to visit the Museum of Contemporary Art. Open every day except Mondays, the museum is home to a staggering collection of work by local and international artists. Highlights for 2025 include exhibitions from Arthur Jafa, Dieter & Bjorn Roth and Wafaa Bilal.
Afternoon: On Lake Michigan
Jutting 1,010 meters out into Lake Michigan, Navy Pier was built in 1916 as a dock for freighters and passenger steamers crossing the lake. Earning its name after being taken over by the U.S. Navy during the Second World War, today’s Navy Pier is one of the Windy City’s most loved attractions and a highlight of this 3 day Chicago itinerary.
The ideal place to pick up some souvenirs, Navy Pier is now given over to countless shops and restaurants. A must for families, interactive Chicago Children’s Museum at the foot of the pier has everything from treehouse trails to a dinosaur exhibition.
For the best views, and a delicious lunch or just a refreshing drink, head to Offshore Rooftop at the pierhead.
This afternoon, see Chicago from a different angle with a cruise on Lake Michigan. Several cruises depart from the dock adjacent to Navy Pier. Thrill seekers will love this half-hour Seadog Speedboat ride, whilst this skyline cruise is ideal for those preferring to soak in the views.
Evening: A Dinner to Remember
Chicago has no shortage of restaurants– in fact, there are over 7,000 in the city, serving every cuisine imaginable. To even scratch the surface, you’d spend your entire 3 day Chicago itinerary reading through them.
That said, for a special dinner that you won’t forget in a hurry, there is one place which really stands out. Beatnik on the River is a Chicago icon.
A wonderful fusion of Mediterranean, African and Mexican flavors, Beatnik’s menu is short, simple and, above all, delicious. With a heavy focus on fresh meat and seafood, highlights include fragrant tagine, prime steak and branzino al pastor. The difficult decision here is not whether to indulge in dessert, but whether the view is even better than the food.
Day 3: Chicago’s Finest Museums
Morning: A Shady Past
You don’t need to know much about the Windy City to associate it with crime. Chicago’s fame for mob rule supersedes even the architecture. Thankfully, Chicago gangsters are a thing of the past, but no three-day Chicago itinerary would be complete without a nod to times gone by.
Kick start your final day by joining this Mob and Crime Tour of Chicago. Follow in the footsteps of Al Capone and John Dillinger as your ninety-minute guided tour takes in Lincoln Park, Harry Caray’s steakhouse and the Biograph Theater.
Afternoon: Around The Loop
Heading south of the river one final time, many of Chicago’s finest museums are located in The Loop. A recent addition to the scene, the American Writers Museum is a must for any literary buff. For those who aren’t squeamish, the Medieval Torture Museum is eye opening if nothing else.
The highlight of the Chicago museum scene, the Art Institute of Chicago is a must for all. Home to pieces from around the world, including Monets and Van Goghs, the highlight has to be Edward Hopper’s Nighthawks.
Evening: Showtime
Chicago’s theater district is mainly concentrated on The Loop’s stretch North Michigan Avenue, although a couple of venues are on the Magnificent Mile. Start your night early with a tour of the iconic Chicago Theater before a relaxed pre-theater dinner at Petterino’s. One of Chicago’s top Italian restaurants, whether you’re craving stone-baked pizza, juicy steak or fresh seafood, you won’t be left hungry.
Broadway in Chicago hosts an ever-changing line-up of showstopping performances. Highlights for 2025 include Titanique, Moulin Rouge!, Riverdance 30 and Tina- The Tina Turner Musical.
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