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United StatesChicago, United States

Chicago for first-timers

Welcome to Chicago! Dive into the city's vibrant culture and explore must-see attractions. Our expertly curated tours will ensure you make the most of your inaugural visit.
Couple examining a map in a city setting, ideal for first-time visitors.

Top things to do

360 Chicago
360 Chicago
from $27
Chicago River Architecture Cruise Tickets
Chicago River Architecture Cruise Tickets
from $32.50
Willis Tower Skydeck Tickets
Willis Tower Skydeck Tickets
from $42.33
First Lady Cruises Chicago
First Lady Cruises Chicago
from $28
Wendella Cruises Chicago
Wendella Cruises Chicago
from $28
Chicago Architecture Center
Chicago Architecture Center
from $7

Top experiences in Chicago

Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
90-min Chicago River Architecture Cruise by Wendella
Sightseeing Cruises
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 590 ratings.From $45
Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
45-min Chicago River Architecture Cruise by Wendella
Sightseeing Cruises
from
$28
45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 927 ratings.From $28
Free cancellation
Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
Sightseeing Cruises
$45
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.8 out of 5 from 118 ratings.From $45
View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Skydeck Chicago Tickets
Observation Decks
from
$42.33
Skydeck Chicago Tickets. Rated 4.8 out of 5 from 126 ratings.From $42.33
Chicago River cruise boat at night with city skyline in the background.
Chicago at Night: River & Lake Sightseeing Cruise by First Lady
Sightseeing Cruises
from
$50
Chicago at Night: River & Lake Sightseeing Cruise by First Lady. Rated 0 out of 5 from 0 ratings.From $50
Free cancellation
Tour boat on Chicago River with city skyscrapers in the background.
Lake Michigan Cruise
Sightseeing Cruises
from
$32.50
Lake Michigan Cruise. Rated 4.9 out of 5 from 169 ratings.From $32.50
Free cancellation
Family enjoying view from Chicago 360 Observation Deck with city skyline.
360 Chicago Sip & View
Observation Decks
from
$44
360 Chicago Sip & View. Rated 4.2 out of 5 from 17 ratings.From $44
Chicago River cruise with tourists viewing downtown skyscrapers.
Chicago River Architecture Cruise
Sightseeing Cruises
$37
Chicago River Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $37
Selling out fast
Guided group walking under Calder's Flamingo sculpture in Chicago.
Architecture Center Admission with Must-See Chicago Walking Tour
Museums
$35
Architecture Center Admission with Must-See Chicago Walking Tour. Rated 0 out of 5 from 0 ratings.From $35

What our guests say

Caroline H

United States
Couple
2 weeks ago
My 1st time to Chicago, everyone I talked to who'd been there mentioned the Architecture Tour was a must. They were not wrong! The guide was a great mix of really intersting information and light humor so the 90 minutes flew by.

90-min Chicago River Architecture Cruise by Wendella

Julian S

United States
Couple
2 weeks ago
Without a doubt, my best experience in this wonderful city was with Headout! The Skydeck experience was amazing!

Skydeck Chicago Tickets

Gomes L

Group
2 weeks ago
Only a cruise like this one lets you take such beautiful photos of Chicago at night. Beyond the cruise itself, there was a great atmosphere on board thanks to the wonderful crew. I highly recommend it!

Lake Michigan Cruise

Lisa W

United States
Solo
3 weeks ago

+1 more

Very nice overview about the architecture and history of Chicago combined with amazing views from both River and Lake. Tess was an amazing narrator and answered all questions, perfect combination of Information and humor

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

Nephateria L

United States
Solo
May 2026
The experience was more than amazing. I'm from out of town and learned so much about Chicago and its history. The tour guide was phenomenal. The river, the buildings and architecture was beautiful. I would highly recommend going if you haven't.

45-min Chicago River Architecture Cruise by Wendella

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Museums in Chicago
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Combos Tickets in Chicago
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How Headout makes choosing experiences effortless

We curate the best ways to experience

We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

We partner with the best

Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

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We curate the best ways to experience
We partner with the best
All the best options, in one place
Book with complete peace of mind

We've served 51 million+ guests and we are here for you

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Happy customers across 10,000+ experiences

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