Backpack Chicago: Architecture & the Blues

Chicago is the United States’ third largest city. It’s got world-class art museums, enough music and theater to keep you entertained for months, and a gorgeous location on Lake Michigan. But perhaps because it’s in the middle of the country, fewer people backpack Chicago than the great U.S. cities on the coasts.


The Windy City attracts business travelers galore. But thanks to the dearth of tourists, it’s pretty cheap to backpack Chicago. Here’s how to get the most out of your time there while keeping costs low.


1. Time your visit with a music festival


Chicago’s Blues Fest (June) and Jazz Fest (late August/September) are two of the U.S.’s best music festivals in those genres. They bring in heavy-hitting musicians like the Rebirth Brass Band and Gary Clark, Jr. And they’re 100% free!


If you want to backpack Chicago for the music, time your visit for Blues Fest or Jazz Fest
If you want to backpack Chicago for the music, time your visit for Blues Fest or Jazz Fest


Better yet, if you backpack Chicago during a major music festival, you can likely snag tickets to the headliners’ side shows at clubs across the city. After I missed him at Blues Fest, I got cheap tickets to see blues icon Billy Branch at Rosa’s Lounge, a well-known local club. Between his show and a few other sets that followed it, I got about six hours of incredible music for the same price as a 45-minute show in DC.


2. Skip the boat architecture tour — do the River Walk instead


Yes, the boat tours along the river are fun. The guides are entertaining and you’ll learn a lot about the difference between Art Deco and Beaux Arts. But they don’t come cheap — I paid $33 for a 90-minute tour.

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If you’re on a budget, unless you decided to backpack Chicago specifically for the architecture, skip the boat tour.


If you skip the tour, you can still get a feel for Chicago’s skyline by walking along the River Walk. Start at Navy Pier and make your way along the river, past the NBC building, the Wrigley building, and the Corn Cobs. (Lonely Planet Chicago (Travel Guide) has decent descriptions of the buildings.


View from the River Walk
View from the River Walk


When you get to the end of the River Walk, you can continue down the street all the way to the Sears Tower. The highlight of Chicago — all for free! Unless you stop for a drink at one of the cafes along the way, of course.


3. Get your art fix in the streets — or in the neighborhoods


The Chicago Institute of Art is one of the best art museums in the U.S. But it’s $25 per ticket.


If you don’t want to pony up the cash when you backpack Chicago, you can still get a taste of fine art. The Loop (the downtown area) is dotted with street sculptures created by the likes of Pablo Picasso.


Picasso's "Untitled"
Picasso’s “Untitled”


If modern art is more your thing, check out the Chicago Cultural Center. In addition to being an absolutely stunning building, it houses exhibitions from local artists. Admission is free and there are even free tours of the building a couple times a week.


Alternatively, head out to the neighborhoods. The West Loop is particularly well-known for its galleries. Second Fridays are the best time to visit. Or head to Pilsen, the heart of Chicago’s Mexican community. The (free) National Museum of Mexican Art is the largest display of Latino artwork in the U.S. It explores Mexican identity on both sides of the U.S.-Mexico border. A wander through the neighborhood on your way to the museum will reveal incredibly colorful murals — don’t miss it when you backpack Chicago!

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Ready to get started?


It’s easy to get into and around the city when you backpack Chicago. Both airports are accessible on the “L trains” (“L” or “El” stands for “elevated,” as the trains run above the streets). O’Hare Airport is on the Blue Line, which runs 24 hours. A ride into town costs $5 and takes about an hour.


An L train crossing the river
An L train crossing the river


Chicago is a huge, spread-out city. Unless you stick with exploring the Loop, even the most devoted backpackers will find that it’s not super practical to walk everywhere. You can buy a day-pass for the L trains and buses for $10 or single-ride tickets for $3.


There are a handful of hostels to choose from when you backpack Chicago. I stayed at Urban Holiday Lofts and would highly recommend it. It’s one of the best-run hostels I’ve ever stayed in, and it’s located in one of the city’s hippest neighborhoods. The only downside is you’ll have to take a train downtown.


Chicago’s most famous food is the deep-dish pizza. Locals could argue for hours over where to find the best, but the consensus seems to be the Giordino’s and Gino’s East are top contenders. It’s not cheap ($15-$25 for a small), but it’s so filling that a single pizza could last 2-3 meals, and you have to try it once when you backpack Chicago.


A slice of heaven at Gino’s East


If you’re on the hunt for cheaper eats, Sultan’s Market has fantastic falafel for $5. Downtown, Pastoral’s deceptively-simple veggie-cheese sandwich ($7) was out of this world. There are plenty of chain restaurants and food trucks in the area around Millennium Park.

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Questions or tips about how to backpack Chicago? Leave a comment!


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