Travel Shots: Four Perfect Days in Chicago

Have friends visiting and need a plan of action?  

Follow this fabulous itinerary with your own personal adaptations and you are bound to have an amazing time (unless it pours four days in a row, which might be a more apt experience anyway).

If it rains, god forbid:

Do: Head to the Art Institute, Museum of Contemporary Art, Museum of Science and Industry or Field Musem

Dont: Do all of these. Give your brain a break, and see a freaking movie or one of the thousand shows in Chicago.  See list under Day No. 3.

Day No. 1:  Ease into tour-guide mode

Start off slowly with a walk through your neighborhood to acclimate your guests. Point out your favorite local digs so they get an idea of what your little life is like in the big city.

My friends and I started with a walk around Lakeview’s bustling streets, making sure to wonder through the infamous Boystown and stop by Wrigley field for photo ops.

We eventually made our way to Ribfest in North Center, where we dined on world class, moist tender meaty bones.  Definitely suggest scoping out nearby neighborhood festivals and eating while enjoying live bands and friendly crowds.

Do: Fill out your information on every raffle and sweepstakes. You’re bound to win something, right?

Don’t: Don’t think about all the spam emails you’ll probably get in coming months and definitely don’t spill your beer all over passerbyers.

After tiring out your guests, you may prefer a quiet dinner nearby.  If so, try Uncommon Ground or Thai Classic.  If not, order up some Chicago deep dish or Chicago-style dogs and just get it out of the way.

Chicago Style Pizza with a rich tomato topping.Image via Wikipedia


A Chicago-style hot dogImage via Wikipedia

Do: Remember to follow the rules though–no ketchup on your dogs!

Don’t: Pregame Ribfest or deep dish pizza with appetizers.  Completely unnecessary.

Day No. 2:  Views and Brews.
On the second day, try a walk through downtown and maybe a concert or two

If your friends are open to a long walk, take them from the north end of Michigan Avenue, anchored by the John Hancock Center, past the historic Water Tower and over to the west loop. Here, stretch out on a gorgeous rooftop bar such as Zed 541, where you can enjoy raspberry sangria and work on your tan.

To walk off the cajun BLT sliders, make your way over to the Willis Tower.  If it’s open and you’re willing to spend the $20, head up 102 floors or 1,353 feet to the glass sky deck and dont. look. down.

When their necks are just starting to cramp from looking up at that mammoth building (we saved our 20 bucks for another glass of wine), head east toward the lake where you’ll inevitably stumble into a festival in Grant Park or a concert in Millenium Park.

We were lucky enough to make it to the Chicago Blues Festival.  Though it’s free admission, you have to pay for tickets to buy beer, vodka lemonades or a wide array of fried foods.

Do:  Give your extra festival tickets to people waiting in line.  Build up that karma.

Don’t:  Try to give out “free hugs” to anyone unless they open their arms to hug you first.  Trust me.

It’s no foodie paradise, but stretching out on the lawn and watching the Chicago skyline jam out alongside thousands of local music lovers is unbeatable.


After you dance up an appetite, head to one of the city’s fine Italian hole-in-the-wall restaurants such as Mia Francesca or Zagat-rated La Gondala.

This tiny restaurant couldn’t hold more than five four-top tables, but the intimate dining and large portions make for a great venue to catch up with old friends and pass around the killer lobster ravioli and basil gnocchi.

Do: Split a bottle of wine and all of your entrees.

Don’t: Expect to get a cab back to civilization within 10 minutes.

Assuming a bottle or two of Chianti doesn’t knock you out, take your friends to Wrigleyville and see the streets by night.  There are one thousand bars on N. Clark Street. Try Vines for a quiet night with great specials or Casey Morans if you just have to dance.

Day No. 3: Go big or go home.

You’ve been busy giving your guests a great first impression of the city so take the third morning and sleep in.

Let your friends know ahead of time that you don’t dote on any of those 8 a.m “morning” people.  It’s Sunday and that’s ridiculous.

Around 10 a.m. take off your cranky pants and bounce back to being an awesome host by making mid-day reservations on the the Architecture Foundation’s boat tour of the Chicago River.


On a sunny day, this tour is clutch.  You’re sipping bloody mary’s, listening to some tour guide’s bad jokes and seeing the city from an inspiring angle.  Life could be worse.

Chicago’s architecture is rich in history and ambition.  Spoiler alert:  After the Great Chicago Fire in 1871 that burned down every inch of downtown, world famous architects from all over the world stepped up to build the “Second City.”  That’s where the celebrity-spewing improv comedy club, Second City, borrows its name.

Speaking of comedy clubs, Chicago is strewn with great venues for a good laugh.  Try Bye Bye Liver a play that is part skits about drinking, part drinking games with the crowd, Baton Lounge for a drag show or Second City performances. 

Do:  Go to one of these shows. 

Don’t: Pay $35 to go on the architecture tour in the rain.  Big bummer.

So your guests have now seen a few sides of Chicago, but what about something a little saucier? 

Argentinian Steak!!Image by Lisa de Vreede via Flickr

For a great example of ethnic cuisine, try Tango Sur, a candle-lit but casual authentic Argentine steakhouse.  The filet from the specials menu is absurd and leftovers make an easy steak ‘n’ eggs brunch while you recover the following morning from the restaurant’s BYOB policy.

Don’t eat meat? 

I wouldn’t encounter this problem because I try not to associate with vegetarians.  They tend to take themselves too seriously. 

But, if your guests are picky eaters, even a carnivore like yourself can enjoy the completely vegan “reuben” or “barbeque chicken wings” at Chicago Diner on N. Halsted. Seriously, check it out.

Day No. 4: The best day ever

Today is the day that you let your friends do the planning.  What do they need to do before peace-ing out?  

The Lincoln Park Zoo? Okay, let’s do it.  The “gangster tour” followed by a cheezborger at the infamous Billy Goat Tavern. I’m in.   The chocolate tour?  Heck yes.  A Dueling Piano Bar where we can “Howl at the Moon”?  Perfect.

HOWL at the MOON!!!  :-)Image by etgeek (Eric) via Flickr

Give your friends a taste with a lightly structured first three days, then let them have some free reign once they’ve seen the sites. 

Maybe they just want to head to the closest beach.   That’s perfectly fine, if not preferred.

Image via Wikipedia

You should definitely make some suggestions for lunch and dinner though–because they might think they know the lay of the land, but you know as well as I do that there are places on your list you’ve been waiting for an excuse to frequent. 

Like the Purple Pig. This is a great restaurant downtown for a special occasion where you can try some quirky food combinations such as peas, bacon and spearmint or pig shoulder with chicken polenta mashed potatoes.  

They don’t take reservations, though, so either go in for a casual lunch or be ready to wait up to two hours for dinner.

Chicago River and Michigan Avenue bridge by ni...Image via Wikipedia

Or, try Ra for some sushi and sake.  Not into slippery dishes?  Try Reza’s for mediterranean food or Geja’s for fondue.  

With a sprinkling of these activities and flexibility, you really can’t go wrong. Just remember– unless they are shitty friends, they flew to Chicago to see you, not just the city.  

Don’t tire yourself out making tightly wound plans, but do relax and enjoy the wrong turns and missed reservations. Experience Chicago with your friends and it’ll feel like your vacation, too.


Published by

Kate Springer

Freelance writer and editor based in Hong Kong. Contributor at CNN, Forbes Travel Guide, BBC Travel, Fodor's Travel Guide, superfuture, Tatler, and more.

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