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Things to Do in Downtown Chicago | Attractions, Food & Hotels

Things to Do in Downtown Chicago

Best Things to Do in Downtown Chicago

Welcome to InDowntownChicago.com — your local guide to the
best things to do in downtown Chicago. From iconic
downtown Chicago attractions and skyline views to neighborhood restaurants, boutique hotels,
and rooftop bars, we help you discover the
places to go in downtown Chicago that actually fit your trip, your budget, and your style.

Whether you’re a first-time visitor or a lifelong local, you’ll find curated ideas for
family-friendly things to do, romantic nights out, and everything in between.

Local-style tips for the Loop, River North, Riverwalk, Navy Pier, Millennium Park & more.


Attractions & Things to Do

Top Downtown Chicago Attractions & Things to Do

Downtown Chicago packs a lot into a few square miles. Here you’ll find world-famous
downtown Chicago attractions like Millennium Park and “the Bean,” Navy Pier, the
Chicago Riverwalk, Willis Tower, Grant Park, and the Art Institute of Chicago — all within easy reach.

Our guides highlight the must-see tourist attractions in downtown Chicago, plus
free things to do in downtown Chicago year-round, so you can build a great itinerary
without wasting time or money.

Explore public art, river cruises, museums, walking tours, and
things to do in the Chicago Loop, River North, Streeterville, and the South Loop — all
in one place.

Millennium Park & The Bean
Navy Pier
Chicago Riverwalk
Art & Museums

👉 Explore our full guide to the
best things to do in downtown Chicago.

Food & Dining

Restaurants & Places to Eat in Downtown Chicago

If you love food, you’ll never run out of options at
downtown Chicago restaurants, from classic
steakhouses in downtown Chicago and legendary deep-dish pizza to stylish rooftop spots
and cozy neighborhood cafés.

Our guides highlight some of the best restaurants in downtown Chicago for every kind of
night out — family dinners, business lunches, quick bites before a show, or a special date. If you’re not
sure where to eat in downtown Chicago, we break it down by neighborhood, price, and style
so you can choose with confidence.

Want river views with your meal? We also feature
the best restaurants in downtown Chicago near the Riverwalk, Navy Pier, and major hotels,
so you can plan dinner around your plans instead of the other way around.

  • Steakhouses, deep-dish pizza, and Chicago classics
  • Family-friendly restaurants with kids’ menus
  • Romantic date-night spots and rooftops with skyline views
  • Cheap eats, quick lunches, and late-night options

👉 Explore our full

downtown Chicago restaurant guide
.

Hotels & Lodging

Best Hotels in Downtown Chicago

Not sure where to stay in downtown Chicago for sightseeing? We break down the
best hotels in downtown Chicago by neighborhood, price, and vibe.

Find the perfect base for your trip with:

  • Boutique hotels in the Loop close to theatres and office towers
  • Luxury hotels in downtown Chicago with riverfront or lake views
  • Family-friendly hotels in downtown Chicago with pools and suites
  • Budget hotels in downtown Chicago near major attractions and transit

Each area guide includes tips on getting around, what you can walk to, and
which hotels in downtown Chicago are best for first-time visitors, couples, or families.

👉 Compare

hotels in downtown Chicago by neighborhood
.

Nightlife & Rooftops

Downtown Chicago Nightlife & Rooftop Bars

When the sun goes down, the city lights up. From laid-back lounges to sky-high patios,
downtown Chicago nightlife has something for every mood.

Our nightlife guides highlight:

  • Rooftop bars in downtown Chicago with skyline views
  • Best bars in downtown Chicago for cocktails, wine, or craft beer
  • Sports bars in downtown Chicago to catch the game
  • Cozy spots that are perfect for a relaxed, romantic night out

👉 Discover the best

rooftop bars in downtown Chicago
.

Neighborhoods & Landmarks

Explore the Loop, River North, Riverwalk & More

“Downtown” isn’t just one place. It includes several neighborhoods and landmark areas, each with its own
feel. Use our guides to find things to do in the Chicago Loop, hidden corners of
River North, and can’t-miss stops
near Navy Pier, Millennium Park, and the Chicago Riverwalk.

We break down:

  • What each neighborhood is known for
  • Things to do near Millennium Park and the Bean
  • Things to do near Navy Pier and along the lakefront
  • Walking-friendly things to do in downtown Chicago without a car

👉 Start with our

neighborhood and landmark guides
.

Trip Planning

How to Plan a Weekend in Downtown Chicago

Need help pulling it all together? Our sample itineraries make it easy to plan
a weekend in downtown Chicago that feels full — not rushed.

Choose from:

  • First-time visitor itinerary – classic
    things to do in downtown Chicago in two or three days
  • Family tripfamily-friendly things to do in downtown Chicago with kids,
    plus stroller-friendly routes
  • Couples’ weekendromantic things to do in downtown Chicago at night,
    plus brunch and photo-worthy stops
  • Budget-friendly weekend – the best
    free things to do in downtown Chicago, low-cost eats, and walkable routes

👉 View sample itineraries (coming soon).

Frequently Asked Questions About Downtown Chicago

What are the best things to do in downtown Chicago for first-time visitors?

Start with the classic downtown Chicago attractions: Millennium Park and the Bean, the
Chicago Riverwalk, Navy Pier, the Art Institute of Chicago, and an observation deck like Willis Tower or
875 N Michigan. Then add a neighborhood walk, a river or lake cruise, and a meal at one of the
best restaurants in downtown Chicago.

Where should I stay in downtown Chicago if I want to be near major attractions?

If you want to walk to as much as possible, look for hotels in the Chicago Loop or
hotels in River North. These areas keep you close to the Riverwalk, Millennium Park,
theatres, restaurants, and transit. Our best hotels in downtown Chicago guides compare
neighborhoods so you can pick the right fit.

Are there free things to do in downtown Chicago year-round?

Yes. You can walk the Chicago Riverwalk, explore Millennium Park, visit
public art and historic buildings, and enjoy seasonal events and festivals. Our list of
free things to do in downtown Chicago year-round helps you build a great trip even on a
tight budget.

What are the most family-friendly things to do in downtown Chicago with kids?

Families love Navy Pier, the Riverwalk, Maggie Daley Park, and the hands-on museums just a short ride
away. We spotlight family-friendly things to do in downtown Chicago with kids, plus
family-friendly restaurants and hotels that make travel easier.

Where can I find the best restaurants in downtown Chicago near the Riverwalk?

The Riverwalk and the surrounding streets are packed with options. Our
downtown Chicago restaurant guides include
best restaurants in downtown Chicago near the Riverwalk for every budget — from quick
bites to special-occasion dinners with river views.

These answers are meant as a starting point — always check current hours, tickets, and reservations before you go.

InDowntownChicago.com is your independent, locally-focused
downtown Chicago travel guide, created to help visitors and locals discover the
best things to do in downtown Chicago, where to eat, where to stay, and how to enjoy the city like you live here.
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