Plan your trip to

Chicago, USA

Discover Chicago

America's third-largest city is known for its soaring skyline, lively lakefront, and world-class museums

Chicago is a city where soul meets grandeur, with soaring architecture mirrored in Lake Michigan, and neighborhoods alive with culture and pride.

The vibe is bold, hardworking, and full of heart, where blues riffs spill out of basement bars, locals argue about pizza like it’s a civic duty, and every season brings its own kind of magic, from snow-dusted skylines to summer street festivals.

History lives in its steel and soul, from the Great Fire to the stockyards, from jazz age legends to civil rights landmarks, with stories etched into brick walls, bronze statues, and the faces of the people who call it home.

The food scene is hearty, creative, and fiercely local. You can dig into a loaded Italian beef, savor Michelin-starred tasting menus, grab tamales on the El, or explore endless flavors in Chinatown and Pilsen, and along Devon Avenue.

Whether you're strolling the Riverwalk, cheering at Wrigley, or dancing to music in Millennium Park, Chicago feels alive with a constant rhythm.

Why we love Chicago

Why we love Chicago (1 of 5)
Chicago is a city where bold architecture, deep history, and big personality come together, with soaring skyscrapers, glittering lake views, and neighborhoods that each feel like their own little world.
The vibe is confident, creative, and no-nonsense, where art and grit go hand in hand — think jazz clubs in basements, mural-covered alleys, and locals who will passionately defend their favorite pizza joint.
History runs deep here, from the legacy of the Great Fire and the rise of the Chicago blues to civil rights landmarks, immigrant stories, and iconic sports moments that still fuel neighborhood pride.
The food scene is hearty, global, and totally obsessed with flavor, whether you’re biting into a loaded Chicago dog, savoring mole in Pilsen, brunching hard in Logan Square, or grabbing Michelin-starred bites in West Loop.
Whether you’re biking the Lakefront Trail, catching a show at Second City, or wandering the Art Institute with a coffee in hand, Chicago feels dynamic, grounded, and full of character — a city that never tries to be anything but itself.

Chicago at a glance

When to go

fallAvg temp62° / 32°
springAvg temp70° / 38°

Safety

World Peace Index rankingEqualdex score

Getting There

Chicago's O'Hare is one of the world's largest and busiest airports, a hub for United Airlines and American Airlines and a major international destination. The smaller Midway airport is a hub for Southwest Airlines and primarily serves domestic flights. Amtrak also offers 14 U.S. train routes that stop in Chicago, from cities that include Los Angeles, New Orleans and Miami.

Chicago airports

  • Chicago Midway AirportMDW
    17km / 11mito city center
    TaxiCity busSubway
  • ORD
    km / mito city center
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Chicago flight trends

Analysis based on point.me exclusive flight data

Average fares

economy class

1.6¢/pointFare value

Typical cash

$334

Typical points

21,000pts

Lowest points

21,000pts
Average fares

business class

1¢/pointFare value

Typical cash

$645

Typical points

62,250pts

Lowest points

62,250pts

Recent award fares to Chicago

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  • Charlotte (CLT)Chicago (ORD)

    Dec 23, 2026first | non-stop
    4d ago
    $304 Cashabout9,000 pts

  • New York (EWR)Chicago (ORD)

    Nov 16, 2026first | non-stop
    4d ago
    $318 Cashabout9,000 pts

  • Boston (BOS)Chicago (MDW)

    Nov 24, 2026business | multi-stop
    4d ago
    $277 Cashabout18,100 pts

  • New York (JFK)Chicago (ORD)

    Dec 04, 2026business | non-stop
    4d ago
    $264 Cashabout23,000 pts

  • New York (LGA)Chicago (ORD)

    Dec 04, 2026business | non-stop
    4d ago
    $319 Cashabout25,200 pts

  • Tampa (TPA)Chicago (MDW)

    Oct 27, 2026business | multi-stop
    4d ago
    $555 Cashabout28,700 pts

  • Los Angeles (LAX)Chicago (ORD)

    Nov 03, 2026economy | multi-stop
    4d ago
    $89 Cashabout4,400 pts

  • Philadelphia (PHL)Chicago (ORD)

    Dec 03, 2026economy | non-stop
    4d ago
    $142 Cashabout4,500 pts

  • Detroit (DTW)Chicago (ORD)

    Oct 15, 2026economy | non-stop
    4d ago
    $300 Cashabout4,500 pts

  • Baltimore (BWI)Chicago (ORD)

    Dec 17, 2026economy | non-stop
    4d ago
    $182 Cashabout4,500 pts

Explore Chicago

Chicago is packed with amazing things to see and do, but here are five top must-dos to get that true Chicagoan experience.

Architecture cruise
Grant Park
Take the L around the world
Discover Chicago’s Black culture
Wrigley Field

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Frequently asked questions

  • How many days is enough for Chicago?

    Three days will give you time to visit the top museums and sights in Chicago, while five days or more will enable you to explore the city's many neighborhoods and restaurants.

  • When is the best weather in Chicago?

    Spring (April-May) and fall (September-October) have mild weather, with warm days and cool nights.

  • When is the cheapest time to go to Chicago?

    Hotel rates and flight fares tend to be at their lowest in winter, from November to March, when temperatures plunge into the 20s and 30s, winds make it feel colder, and snow is common.

  • How far is the Chicago airport from the city?

    The city's main airport, ORD, is about 18mi (29kms) from the city center, accessible via taxi, subway, or city bus, in about an hour.

  • Is Chicago safe?

    Chicago is generally considered a safe city, though it is a major metro area that sees a lot of tourists, so you should exercise caution and keep your eyes on your valuables, especially at night or in crowded areas.

  • Do I need to rent a car in Chicago?

    A car is more of a hindrance than a help in Chicago, where parking can be both expensive and a challenge. The L train connects most major neighborhoods, which can then be explored on foot or by bike.

  • Is Chicago expensive?

    As a major city and popular tourist destination, Chicago is on the more expensive side, particularly for hotels. A four-star hotel in the city center will generally run $325-$500 per night.