Full day highlights of Chicago

Nature
The wow factor for nature - does it show nature at its best? Doesn't need to be the wildebeest migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
6
Culture
How much does this experience showcase some of the better and finer things that us humans can offer? Sure, it can be ancient ruins and renaissance churches, but it can also be festivals or soaking up some of the great modern cities of the world
8
Fun factor/activity
Very simple - was it fun? This is usually linked in with doing some kind of activity - i mean, walking along some cliffs is nice, but paragliding from them, now that is fun. Its a vastly underrated factor in a truly great experience
8
Avoid the crowds
Big tour groups and being surrounded by loud fellow tourists can sap the life out of even the greatest of travel experiences. This score is to reflect just how much you can avoid this. But. . . The score also takes into account if the crowds actually add to the experience, such as with a party town or a bustling local market
5
World famous
How world famous is the experience?
8
unique
How hard is it to have a similar experience in other places round the world?
7
Overall TE Score
The overall travel experiences score:  fun factor + avoid the crowds + (best of nature or culture) + (best of world famous or unique). Then convert into a score out of 100
72 *What the scores mean and where do they come from
RANKING
How this travel experience ranks compared to all the other experiences on this site, based on the travel experience (te) score
132nd/454
Top 30%
continent
North America
country
USA
Length of time
1 day or less
Typical daily price
This gives you a rough idea of the daily price based on 2 people travelling where they can split costs like accommodation. It excludes travel there and back, and factors in inflation the numbers in brackets show the price range for the full time of the experience (so not necessarily daily). It is a range to reflect different budget vs higher end
$210 (typically $70 - $360)
Time of year visited
June
Primary Tags
Click on any of the tags to see all travel experiences with the same tag
Big city Cycling Skyscrapers
All Tags
Beach promenade Beaches Boat trip Bridges Cool neighbourhoods Lakes Live sport Music Concert Stadiums
Wow Factor
The wow factor reflects just how much you’re likely to say “wow”. As there’s a lot of experiences in the world, and a lot of wows, i’ve gone with a simple ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️ score, and a separate category for the truly "gash"
⭐⭐⭐

Summary

Winters are brutal, but in the summer Chicago is one hell of a place to be with its lakefront beaches, host of activities and with its general buzzy sassy attitude.  Speaking personally, I had one of the best days of my life in Chicago because I managed to combine a cycle up the lakefront, the boat tour of the sites, a baseball game, concert and drinks.  Chicago in summer is raring to go and I’ve listed my top tips for an amazing day below.

 

Chicago skyline view from the John Hancock Centre

 

Highlights

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#1 Taking a bike an heading north along the lakeshore, built to accommodate cyclists and giving you a range of beaches neighbourhoods to check out on the way

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#2 Riding to the top of the skyscrapers, in what is the original Home of the Skyscraper

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#3 Taking in one of the live sports games - a wonderful way to feel the buzz of the city. In this case, Rigley Field

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#4 The Chicago Architecture Centre Tour - gives you a view and a history of the city from the various rivers that snake their way throughout. Surprisingly engaging

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#5 Heading as far north as Montrose Harbour for a great context view of downtown, and feeling the more spacious take on the city

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#6 Riding the subway around The Loop and feeling, just for a moment, like a local

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#7 Visiting the lakeside beaches that are all along the beautiful lakeshore. A really gorgeous benefit of living in the city

Travel Tips for a first-timer

Be sure to jump on a bike and cycle up the lakeshore – easy to get a Divvy Bike at various places along the lakeshore, and cycling is a perfect way to see a city.  I went as far north as Montrose Harbour, which is only 7.5miles / 12km from the city centre, but gives some great panoramic views on downtown, plus . . .

Take the opportunity to cycle into some of the neighbourhoods by the lakeshore – it’s nice to see how the rich Americans live!

See if you can take in one of the sports games, or maybe one of the concerts – I was lucky enough to see the Cubs play at Wrigley Field, but also U2 at Soldier Field on the same day.  It wasn’t so much the performances themselves, but more little things like the buzz of walking to the venues, meeting new people also full of energy, and the overall novelty of some of it.  Worth checking to see what’s on and taking advantage of these spectacles that a major city like Chicago has on offer.

Take the Chicago Architecture Centre Tour – it leaves from the river dock and makes its way through the inner waterways, allowing you to take in the various skyscrapers and general sites of the city from a different view to the street.

Head up to the viewing floor of the John Hancock Centre for some truly stunning views across the city.

Take the subway around The Loop – it was so enjoyable just watching the city go by and feeling for just a moment like a local.

Wander through Navy Pier – its super accessible as you cycle along the lakeshore.

Experiences nearby

The below map shows experiences nearby with a colour that reflect the Overall Score of those experiences

Other World-class City Experiences

London’s top 10 in summer
⭐⭐⭐

Beijing highlights for 2 days – 10 tips
⭐⭐⭐⭐

3 days for Buenos Aires
⭐⭐⭐⭐

The tourist highlights of Rio de Janeiro
⭐⭐⭐⭐

3 Days in Budapest – Baths, Architecture and Ruin Bars
⭐⭐⭐⭐

Seeing the spectacular sights of Dubai
⭐⭐⭐

2 days for the classic highlights of Hong Kong
⭐⭐⭐

Melbourne city break
⭐⭐

Munich Christmas Markets, Beer Halls and visiting Neuschwanstein Castle
⭐⭐⭐⭐

Classic highlights of Paris
⭐⭐⭐

2 days in Singapore
⭐⭐

A week in Cape Town
⭐⭐⭐⭐⭐

Score Detail

The scores above are the real point of this site.

Over 20+ years and 100+ countries, I’ve tried to rank the world’s best travel experiences — from genuinely mind-blowing ⭐⭐⭐⭐⭐ to the properly gash.

Every one of the 500+ places on this site has both a Wow Factor rating and a more analytical Travel Experience (TE) score based on the things that actually make travel memorable.

If you're curious about the thinking behind it, head to the About page.

Otherwise, explore the map above or on the Home page and see which places truly deliver maximum wow.

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