Travel Tips

Experience Obama’s City: Travel Tips for a Barack-Style Chicago Vacation

Locations in this article:  Chicago, IL

Now-President ObamaAs President Obama waves goodbye to Chicago and says hello to Washington, DC, visitors continue to come in droves to experience the Windy City, Barack-style.

The inauguration may have brought the crowds to the nation’s capital, but the new President’s hometown of Chicago caught Obamamania long ago.

Whether you take an organized tour or go at it on your own, here are a few hometown spots of Obama’s that shouldn’t be missed.

Obama’s Old House1. 5046 South Greenwood Avenue
High security keeps crowds away from the Obama’s tony Kenwood neighborhood mansion, but here’s a bird’s-eye view of the President’s Chicago home via Google Maps. It may be the closest the Secret Service lets you get.

2. Get Your Hair Cut in Chi-Town
Hyde Park Hair Salon & Barber Shop
Only in Obama’s Chicago does a barber shop become a tourist attraction. President Obama stuck to his roots (literally) at his favorite local barbershop. Make sure to ask for Zariff, who has been doing his do for the past 15 years, and ask for the “Obama style” which is now all the rage. If you’re lucky, you may even sit in his favorite chair.

Obama next3. Take It Out On the Court
East Bank Club
Forget about snagging Obama’s favorite treadmill or taking his spot in spinning class.

President Obama is a true-blue basketball fan and could often be seen playing a pick-up game on the courts. He was spotted releasing some stress during the campaign during a pickup game on the Hayes Drive courts as well.

4. Study Up on the New President
57th Street Books
Still haven’t bought your Obama autobiography? Forget Amazon and pick it up at 57th Street Books, a reportedly Obama’s favorite bookstore. As longtime co-op members, the Obamas even celebrated the release of Dreams of My Father and The Audacity of Hope at this unassuming little book store.

5. Dine Like an Obama
Obama eats Whether it’s New American cuisine or down-home Chicago-style pizza, the Obamas know how to eat. Check out Chef Rick Bayless’ upscale Mexican eatery Topolobampo ( and order the sopa azteca. President Obama has admitted that he’s in love with the soul food at Mac Arthur’s family restaurant. (

Medici’s on 57th, a restaurant and bakery located near the University of Chicago, is another longtime favorite of Barack and Michelle (you’ll know you’re in the right place when you see the “Obama Eats Here” T-shirts). Order the “garbage pizza” loaded with anything and everything you can imagine.

And for a special occasion, head to the South Shore Cultural Center, where the Obamas held their wedding reception. Overlooking the shores of Lake Michigan, its signature restaurant, Parrot Cage Restaurant, features a rather pricey seasonal menu, but offers a reasonable $25 prix fix menu every Wednesday and Thursday evening.

Want more ideas on how to experience Obama’s Chicago? Visit Choose Chicago’s Presidential Chicago page.

By Michelle Castillo for

Like politics? Don’t miss Traveling Joe Biden’s Delaware as well as Sarah Palin Vacations: From Snowmachines to Moose Hunting, Travel Like a Palin.

For more fun in Chicago, we’ve also got an Off the Brochure Travel Guide: Chicago, Illinois.

Want more Washington, DC travel information? Try these articles: