Full day highlights of Chicago

The wow factor for nature - does it show nature at its best? Doesn't need to be the wilder-beast migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
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
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
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 food market
World famous
How world famous is the experience?
How hard is it to have a similar experience in other places round the world?
Overall Score
The highest score of nature or culture, + fun factor, + avoid the crowds, + the highest score of world famous or unique. Then turned into a score out of 100. More details at the bottom of the page
72 *What the scores mean and where do they come from
North America
Length of time
1 day or less
Rough cost
Obviously people have different tastes, so this will depend on those tastes, but this is a rough idea of price of the whole experience based on 2 people able to split the accommodation costs and excluding travel there and back
$ 250
Time of year visited
Primary Tags
Click on any of the tags to see all travel experiences with the same tag
How this travel experience ranks compared to all the other experiences on this site
104th/372 This travel experience's ranking compared to all the other experiences on this site
Top 30% SUMMARY RATING: Superb


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.  I, from a personal point of view, 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 in the Tips section below


#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

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

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

#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

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

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

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

Travel Tips

  • 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

Score Detail

Background - how many times have you asked someone what a travel experience was like and the response was "amazing" or "awesome"?  That response is nice to know, but it makes it hard to differentiate that experience compared to others.  That is exactly what these scores are trying to do - differentiate the experience by giving a score out of 10 based on 6 categories and then giving an overall experience score

This overall experience score is calculated by:  take the highest of the "Culture" or "Nature" score (1-10) + "Fun factor" (1-10) + "Avoiding the crowds" (1-10) + highest of the "Unique" or "World Famous score" (1-10).  Then convert into a score out of 100

Extra detail - the logic being that I find all of the 6 individual scores important, but I don't want to mark an experience down just because it doesn't cover both "Culture" and "Nature", or because it isn't both "World Famous" and "Unique".  Take the examples of Safari in The Serengeti and walking through Rome - they both appeal at opposite ends of the nature / culture spectrum, and you can have a fantastic time without needing to appeal to both sides.  So, their overall scores aren't penalized for their lack of one or the other, and I've done the same for "World Famous" vs "Unique".  But . . . I do think that the "Fun factor" of an experience is important, irrelevant of other factors, and so is "Avoiding the Crowds" (or where there are crowds that add to the experience).  So, both of these scores are standalone