Chicago, United States travel guide

The birthplace of the skyscraper, where bold architecture lines the river and Lake Michigan meets a deep-dish, blues-soaked culture.

Best time to visit: May-June and September-October
Average daily budget: $140 to $260 USD
Ideal trip length: 3 to 4 days

Chicago is the great American architecture city: the skyscraper was born here, and the best way to understand it is from a boat on the river looking up. Add a lakefront of beaches and trails, world-class museums, a legendary music and comedy scene, and deep-dish pizza, and you have one of the most underrated big cities in the country. Joy Plus times the architecture river cruise, sequences the museums and the lakefront, and finds the blues bars and pizza spots that locals swear by.

Chicago itinerary

Day 1, Get oriented

Morning: Architecture river cruise. The single best Chicago experience: a guided boat tour explaining the skyline from the water.

Afternoon: Explore The Loop, The downtown core: skyscrapers, the elevated 'L' train, Millennium Park and the Art Institute.

Evening: Millennium Park & Cloud Gate. See 'The Bean', stroll the gardens and catch a free concert at the Pritzker Pavilion.

Day 2, Go deeper

Morning: Skydeck or 360 Chicago. Ride up Willis Tower or the John Hancock for vertigo-inducing glass-ledge views over the lake.

Afternoon: Explore River North & Magnificent Mile, Galleries, dining and the famous shopping strip of Michigan Avenue.

Evening: Art Institute of Chicago. One of the world's great museums, home to Hopper, Seurat and an unmatched Impressionist collection.

Day 3, Hidden side

Morning: Millennium Park and the Bean. See your reflection in Cloud Gate ('the Bean'), then explore the lakefront, Art Institute and the deep-dish pizza and hot dogs that define the city.

Afternoon: Explore Wicker Park & Bucktown, Hip neighbourhoods of indie boutiques, music venues, cafes and street art.

Evening: The 606 elevated trail, a former rail line turned park through the northwest neighbourhoods.. A local favourite most visitors miss, worth the detour.

Best neighbourhoods

The Loop: The downtown core: skyscrapers, the elevated 'L' train, Millennium Park and the Art Institute.
River North & Magnificent Mile: Galleries, dining and the famous shopping strip of Michigan Avenue.
Wicker Park & Bucktown: Hip neighbourhoods of indie boutiques, music venues, cafes and street art.
Pilsen: The Mexican-American heart: vibrant murals, taquerias and the National Museum of Mexican Art.

Must-do experiences

Architecture river cruise: The single best Chicago experience: a guided boat tour explaining the skyline from the water.
Millennium Park & Cloud Gate: See 'The Bean', stroll the gardens and catch a free concert at the Pritzker Pavilion.
Skydeck or 360 Chicago: Ride up Willis Tower or the John Hancock for vertigo-inducing glass-ledge views over the lake.
Art Institute of Chicago: One of the world's great museums, home to Hopper, Seurat and an unmatched Impressionist collection.
Architecture river cruise: The best way to grasp Chicago's legendary skyline, a boat tour along the river with an expert guide explaining the iconic buildings. A must-do that locals recommend.
Millennium Park and the Bean: See your reflection in Cloud Gate ('the Bean'), then explore the lakefront, Art Institute and the deep-dish pizza and hot dogs that define the city.

Hidden gems

The 606 elevated trail, a former rail line turned park through the northwest neighbourhoods.
The murals and taquerias of Pilsen, far from the tourist trail.
Free Tuesday-evening jazz at the Chicago Cultural Center under its Tiffany dome.
The Garfield Park Conservatory, a vast, free Victorian glasshouse west of downtown.

Daily budget

$140 to $260 USD per day.

What to eat

Deep-dish pizza, the towering Chicago classic
A Chicago-style hot dog, dragged through the garden
Italian beef sandwich, dipped and spicy
Tacos and tamales in Pilsen

Getting around

The CTA runs the elevated 'L' trains and buses across the city; a Ventra card or contactless tap covers both, and the 'L' is the easiest way around downtown and to both airports. The Loop and lakefront are walkable, and the lakefront trail is great for cycling. Uber and Lyft are everywhere. The Blue and Orange 'L' lines link O'Hare and Midway airports to downtown cheaply.

Safety

The central, tourist-focused areas (the Loop, Magnificent Mile, lakefront and North Side neighbourhoods) are safe and well-policed. As in any big city, stay aware on transit at night and avoid wandering into unfamiliar South and West Side areas after dark. Winters are bitterly cold and windy, so dress in serious layers.

Frequently asked questions

How many days do you need in Chicago?

Three to four days covers the architecture cruise, Millennium Park, an observation deck, the Art Institute and a couple of neighbourhoods, with time for the lakefront.

Is Chicago good for solo travellers?

Yes. The central neighbourhoods and lakefront are safe and walkable, the 'L' makes getting around easy, and there's endless food, music and culture for solo days.

When is the best time to visit Chicago?

Late spring and early autumn offer mild weather and outdoor festivals. Summer is warm and lively along the lakefront; winter is famously cold and windy.

Is the Chicago architecture river cruise worth it?

Absolutely. It's widely considered the best way to experience the city, with expert guides explaining the skyline from the water. Book ahead in summer, as the popular operators sell out.

How do I get from the airport to downtown Chicago?

The CTA Blue Line connects O'Hare to downtown and the Orange Line connects Midway, both cheaply in 30 to 45 minutes. Taxis and rideshares are faster but considerably pricier, especially from O'Hare.

Is Chicago safe for tourists?

The downtown, lakefront and North Side neighbourhoods that visitors frequent are safe and busy. Use normal big-city awareness on transit at night and stick to well-travelled areas, as crime is concentrated in specific neighbourhoods away from the tourist zones.

What food is Chicago famous for?

Chicago is famous for deep-dish pizza, Chicago-style hot dogs (never with ketchup), and Italian beef sandwiches. The city also has a superb fine-dining and global-food scene, especially in neighbourhoods like Pilsen.

Is Chicago worth visiting?

Yes, for world-class architecture, museums, the lakefront, food (deep-dish pizza, Italian beef), music (blues and jazz) and a friendlier, more relaxed big-city feel than NYC.

When is the best time to visit Chicago?

Late spring to early autumn (May-October) for warm weather, lakefront life and festivals. Winters are bitterly cold and windy, hence 'the Windy City', though the holiday season is festive.

How do I get around Chicago?

The 'L' elevated train and bus system (use a Ventra card) covers the city well and links both airports. Downtown and the lakefront are also very walkable and bike-friendly.

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