New to Chicago? Welcome to this amazing city! You’re going to love living here.
But a quick warning to all you lovely British noobs, if you’ve just moved here in late summer, you’ve only got a few weeks left before the summer seasonal fun shuts down and we start heading towards that infamous bitter cold! And that cold sets in until April!
It might surprise you but throughout the USA (OK maybe not California!) the end of summer has a specific deadline and that deadline is Labor Day weekend, the first weekend in September. This is the date when most of the summer fun closes and the brief but awesome Autumn begins.
So here is a head start on how to make the most of the next ten weeks. Don’t take a single second of sunshine for granted. Save those indoor museums and restaurants for the chilly months and get the following done quickly whilst you can!
1. The Chicago Architecture Foundation Riverboat Tour
Always my number one recommendation come rain or shine but definitely more pleasant during the sunny months. The story of Chicago can be told through its stunning skyline and no one tells the story as well as the CAF volunteers. Prepare to be amazed and bring a camera.
2. Drink on a roof top bar
Yes, some of these do now stay open in winter and have little fire pits and heaters on them but you’ll be bonkers to be out there for long when the weather hits minus 10c. The Trump is always an especially good choice, as is the new Virgin Hotel rooftop bar, Benchmark, The Wit and J Parkers.
3. Sunday Brunch up The Hancock
This is all year round but leave it too late and you’ll be staring out at a frozen tundra rather than the beautiful blue covered in sail boats. Sit in one of the corners and you’ll feel like you’re floating in the middle of it!
4. Race Along the Lake in The Seadog
Another seasonal adventure that closes. This is high adrenaline fun zip along the lake shore
5. Get to a beach
Lakes can have big sandy beaches? Of course they can if you’re in Chicago! But they close after Labor Day so go enjoy one quickly.
6. Kayak down the river
Sunset tours are very popular through until September. The guides are funny and the views are magnificent.
7. Seasonal Eats
Yes even some of the food here has a date limit! This is the time to get to an outdoor farmers market and fill up on Midwestern apples, peaches and corn, corn, corn.
8. Visit a Farm
Apple picking and “pumpkin patches” are all-American traditions that come into their own in the Midwest. Unlike the year-round British garden centres, Midwestern farm shops are seasonal and tend to close after Thanksgiving at the end of November. Favourites include Goeberts.
9. Enjoy Movie or Music Outside in a Park
Google your local Parks and Recreation Department, they exist to help you eek every last ray of outdoor sunshine from the next three months. The Grant Park music festival is free and runs until Labor Day. There is also the Ravinia Festival.
10. Splash Parks and Fountains
Chicago has some beautiful fountains to play in including the Crown Fountain in Millennium Park with its spotting faces and the famous Buckingham Fountain which has a light show (and was built by a Brit!). The fountains get drained ready for winter in October.
The latest addition to Chicago’s many water based fun is in Maggie Daley Park, a Park built just for kids. Although the park is open 365 days a year, the climbing wall and splash pads will be off limits once they are frozen!
11. Explore nature in the Botanical Gardens or Arboretum or drive to Michigan!
Early September is a beautiful time in Chicago as the leaves start to change. The Botanical Gardens and Morton Arboretum are two great places to experience this all-too-short season. Do you know there is a “leaf forecast” like a weather forecast but for leaves? Michigan has better colour than Illinois, maybe put a weekend aside for a short road trip.
12. Navy Pier Fireworks
Navy Pier does an incredible fireworks show set to music every Wednesday and Saturday night at 10pm until – yes you guessed it! – Labor Day weekend!
WHAT HAVE I MISSED? WHAT ELSE SHOULD BE ON THIS LIST?
Bonus tip, September is a great time to think about planning a holiday somewhere warm in February or March. Remember you’re now only a couple of hours flight from the Caribbean and Mexico! You can even travel to Puerto Rico using your USA drivers licence. Lots of great holiday offers in the Labor Day sales.