TrekAmerica’s
City Guide to
CHICAGO
CHICAGO
OVERVIEW
Sitting on the Southern shore of Lake Michigan, Chicago
has made a name for itself as a cultural hub, with bold
architecture and seriously impressive skyscrapers. The
iconic Willis Tower offers incredible city skyline views, or
explore closer to ground as you stroll the streets.
One of the largest cities in the U.S., there’s plenty to
see and do. By day, explore the renowned museums and
sprawling park spaces, and by night devour delicious food
and soak up live music and a vibrant bar scene.
DON’T MISS!
1. WILLIS TOWER
Offering spectacular views spanning up
to four states – and The Ledge, a glass
balcony extending four feet outside the
103rd floor!
6. GRACELAND CEMETERY
The resting place of many notable
Chicagoans, you’ll see see some
of the country’s most intricate
memorial architecture.
2. LINCOLN PARK
For calm in the concrete jungle – find
gorgeous green spaces, restaurants,
nightlife and history.
7. ART INSTITUTE OF CHICAGO
Home to more than 300,000 works,
check out one of the oldest and largest
art museums in the United States.
3. BOBBY’S BIKE HIKE
Pedal your way through lakefront
neighbourhoods and Southside ‘mob
hangouts’.
8. BASEBALL STARS
Chicago is home to two major baseball
teams, Cubs and White Sox, as well as
football and basketball teams.
4. CHICAGO CULTURAL CENTER
Gaze up at the jaw-dropping stained
glass dome, see ornate mosaics and
take in one of the many free cultural
events daily.
9. CHICAGO DEEP DISH PIZZA
Any visit to Chicago isn’t complete
without getting your hands on this
notorious city specialty – super deep
pan with loads of toppings!
5. MOVIE LOCATIONS TOUR
From The Dark Knight to Ferris
Bueller’s Day Off, explore some of
Chicago’s famous movie locations.
Book at freetoursbyfoot.com.
10. CHICAGO HISTORY MUSEUM
Founded in 1856, delve into the city’s
history with the museum’s engaging
exhibits, telling stories from Chicago
past and present.
THINGS TO DO FOR FREE
1. L
incoln Park Zoo – One of the few free zoos
left in the country, it’s home to around 1200
animals, including lions, apes, crocodiles and
pandas.
2. G
arfield Park Conservatory – Wander
through beautiful surroundings at one of the
largest and most stunning conservatories in the
country.
Lincoln Park Zoo
3. M
axwell Street Market – Haggle your
way around this Sunday market, picking up
anything from fresh produce to a new outfit
– and don’t miss the Mexican and Latin street
food stalls!
4. Navy Pier – Way more than your local seaside
town stretch, Navy Pier is home to restaurants,
bars, a park and the eye-catching Centennial
Wheel.
Chicago History
Museum
5. Montrose Beach – Beaches might not be the
first thing that spring to mind when you think of
Chicago, but Montrose is Chicago’s largest and
best sandy spot.
Navy Pier
Garfield Park
Conservatory
Chicago
Theatre
Willis Tower
Best Selfie Spots
Cloud Gate – Because if you don’t get a snap of this iconic
reflective sculpture, did you really even visit Chicago?!
360 Chicago Observation Deck – Make your selfie
stand out with awe-inspiring 360 degree views of the city to
be seen – or hang over the edge of the building
with the gravity-defying Tilt attraction!
Route 66 sign – Ever wanted to road trip
down the iconic Route 66? Get your picture
taken where it all begins, at E. Adams St., just
west of S. Michigan Ave.
I spy…
One of the more unusual
shops in the city, Wicker Park
Secret Agent Supply Co. is the
perfect place to pick up a whole
range of spy essentials.
FOR THE FOODIES
From Chicago’s all-American staples to fine dining,
the city has plenty on offer to satisfy even the biggest
appetites.
Our favourites:
1. Pequod’s Pizza (2207 N Clybourn Ave, IL 60614) –
Load up on cheese and delicious toppings at one of the
locals’ favourite pizza spots in the city, in the buzzing
Lincoln Park area.
2. Portillo’s (100
West Ontario
Street, IL 60654) –
This South Beach
institution focuses
on good old
fashioned soul food, like chicken and
waffles, mac and cheese, and shrimps
and grits, but delivered in an upscale
and pretty impressive way. Meals are
huge so aim to share!
3. Bad Hunter (802 W. Randolph St., IL 60607) – It’s
not all meat feasts and deep dish! Bad Hunter is a perfect
eatery for non-carnivores
and curious tastebuds alike,
creating enticing veg-based
dishes.
Toilet Talk
In terms of odd artwork,
Sh*t Fountain really takes the
you-know-what. A sculpture of
a giant turd on a 3ft high plinth?
Alright then, Chicago.
Nightlife
If you want to hear some original tunes, check out
Phyllis’ Musical Inn - Wicker Park’s first live-music
venue, with a low tolerance for cheesy covers. At
Lincoln Hall, check
out the newest up-andcoming names before
they make it big.
Fancy dinner with a
side of jazz? Andy’s
Jazz Club and
Restaurant is a casually
sophisticated way to
spend an evening. The
House of Blues also offers
music alongside Southerninspired dishes such as po’
boys & jambalaya.
For comedy fans, pay a visit
to Second City, which launched the careers of stars
including Bill Murray, Tina Fey and Steve Carrell.
At Laugh Factory and The Comedy Bar, hometown
talent rules.
As for the club scene, you could dance the night
away at Smart Bar, where cutting-edge DJs play
house, techno
and electro on the
weekend. Or if you’re
after some quirky
nostalgia, check out
Berlin (the Chicago
dance spot, that is).
FESTIVALS & EVENTS
JUNE-AUGUST – Millenium Park’s
Summer Music Series offers up a
whole host of genres in the Jay
Pritzker Pavilion – and it’s all free!
AUGUST – Sing along at the top of
your lungs to the best buzz bands and
pop stars in Grant Park at
Lollapalooza, with four epic
days of music.
Watch
out for...
SEPTEMBER – Chicagodwellers flock to Union
Park for the North
Coast Musical Festival,
featuring the best in
electronic music. More
into rock and punk?
Check out Riot Fest, also
in September.
Central Chicago is a pretty
welcoming place, but avoid
heading out into some of the more
suburban areas, where violent
crime rates can be higher.
Contact details – website and
international Tel no in the footer.
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