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Chicago

Lakefront skyline views, deep-dish & blues bars

Browse Chicago

Chicago is one of the most rewarding places to explore, and this local guide brings together the best things to do, where to eat and where to stay in one place. Highlights include Skyline View from Adler Planetarium, Millennium Park and Navy Pier. Food lovers should not miss Lou Malnatis and Portillos. Below you will find 12 hand-picked local recommendations across sights, restaurants, hotels and tours, which you can filter by category and budget to plan the perfect trip, whether you have a weekend or a week.

Chicago at a glance

  • Ideal stay: 2 to 3 days
  • Best time to visit: spring and autumn
  • Highlights: Skyline View from Adler Planetarium and Millennium Park
  • Where to stay: River and Loop
  • Local picks: 12 hand-chosen recommendations
  • Getting around: walkable, plus easy public transport

Local tips for Chicago

Stories and neighbourhood know-how from our local guides.

Where to stay in Chicago

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North Lawndale

beelove café

Why it matters: this North Lawndale cafe is run by Sweet Beginnings, a social enterprise of the North Lawndale Employment Network that hires and trains formerly incarcerated residents, sweetening its drinks with honey from its own urban apiaries. It occupies the striking glass-fronted former home of the Community Bank of Lawndale, once the area’s first Black-owned bank. Order the honey latte made with beelove raw honey, and pick up a jar or honey-based skincare to take home. Weekdays 7am-4pm, Saturdays until 2pm.
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River North

Lou Malnatis

The classic destination for Chicago deep-dish pizza.
★ 4.6
$$
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River North

Portillos

Chicago-style hot dogs and dripping Italian beef sandwiches.
★ 4.5
$
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From our home city

Visiting New York City on this trip?

This guide is made by the team behind Like A Local Tours - NYC's award-winning, woman-owned food tour company. If New York is on your route, eat through it with us.

Before you go

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Book your trip to Chicago

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Chicago travel FAQ

How many days do you need in Chicago?

Two to three days is enough to enjoy the highlights of Chicago at a relaxed pace.

Where is the best area to stay in Chicago?

Stay central and walkable to the main sights for a first visit.

What are the best things to do in Chicago?

Browse the local picks above, from top sights and museums to where to eat and stay. Or read our best things to do in Chicago guide.

What is the best time to visit Chicago?

Spring and autumn usually bring the most comfortable weather and thinner crowds, though Chicago is worth visiting year-round.

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