Chicago is a must-see destination whether you’re on a journey around the world or simply looking for a weekend getaway. With its signature hot dogs, deep-dish pizza, blues clubs, and comedy scene, the Windy City is a whirlwind of food and culture that’s not to be missed. If you’ve only got two days in Chicago, this guide will help you hit the highlights and make the most of your time.
Stay: HI Chicago Hostel - Conveniently located downtown, near stops on all L lines in the Loop.
Chicago has two major airports, Midway and O’Hare, and both are located on the city’s metro (or “L”) lines. A single ride fare is between $2.50-$5.00, depending on which airport you’re flying into, and will get you all the way into the Loop. We recommend taking the L a few times in this guide, so you might consider buying a multi-day pass to save some cash.
Head down to the hostel’s second-floor common area for HI Chicago’s weekly Welcome Party. Enjoy some free snacks and drinks while you meet other travelers staying at the hostel. Don’t forget your photo I.D. if you’re 21 or older and want to drink alcohol. Now that you’ve made some new hostel friends, it’s time to start exploring the city.
If you’re 21, join the Green Mill Jazz Outing, a volunteer-led hostel tour that goes to the Green Mill Cocktail Lounge. The club is a must for Chicagoans and tourists alike. It has a cozy vibe and is known for its vintage decor and classic cocktails. Since the club doesn’t serve food, you’ll be stopping at Carmela’s Taqueria, a local Mexican restaurant, on the way. There’s a $10-$15 cover charge at the club so be sure to bring cash and a photo I.D.
If you’re under 21, your best bet is to start eating your way through the best of Chicago’s deep dish pizza. Just a few blocks from the hostel you’ll find Lou Malnati’s Pizzeria, one of the oldest and most-well known of Chicago’s homegrown pizzeria empires. It tends to be crowded on weekends, but trust us, it’s worth the wait. If you don’t want to wait, call in your order and bring it back to the hostel to share with other travelers over some games of pool and ping pong. Deep dish is so filling you won’t be able to eat more than a slice or two on your own anyway.
HI Chicago offers free breakfast every single day, so be sure to wake up and make your way to the second-floor dining room before 10 a.m. The spread features cereal, bagels, pastries, and a variety of other tasty items, along with tea and coffee to help you fuel up for the day. It’s a great place to meet other travelers and reconnect with new friends you made the night before. When you’re ready to start exploring, take a left out of the hostel and walk just a few blocks to find Grant Park. Inside Grant Park you’ll find the famous Cloud Gate sculpture. This iconic, mirrored sculpture, affectionately known as “The Bean,” is a must stop for any traveler. Walk around and under to see the many ways this stunning structure reflects the surrounding city. (For a real treat, wake up early and get there at sunrise. You’ll practically have the whole sculpture to yourself and it will be even more beautiful in the early morning light.)
If the weather is nice, explore the many mini parks and gardens that make up this 319-acre park that’s referred to as “Chicago’s Front Yard.” Rent a Divvy bike to cover more ground and continue your exploration along Lake Michigan on the Lakefront Trail. The park also features world-famous attractions, including The Art Institute of Chicago, The Field Museum, Shedd Aquarium, and Adler Planetarium. Check with the hostel staff for discounted tickets before you go.
Take the L Pink Line to the 18th Street stop to explore Pilsen, a historic Mexican American neighborhood full of colorful street art, superb vintage shopping, and some of the best Mexican food you’ll ever try. Stop at the free National Museum of Mexican Art to explore the museum’s spectacular collection of Mexican art and cultural artifacts. Check out the nearby Nuevo Leon Bakery to try some treats from an authentic, self-serve Mexican bakery, or visit one of the neighborhood’s many delicious taquerias. If you’re a music lover, be sure to pop into Pinwheel Records to check out their impressive collection of vinyl.
No trip to Chicago would be complete without a visit to The Second City, the world-famous improv comedy troupe that has launched the careers of dozens of stars, from Bill Murray and Jordan Peele to Gilda Radnor and Tina Fey. Buy tickets for the Mainstage or UP Comedy Club online in advance for as little as $18 and then hop on the Brown or Purple Line to the Sedgwick stop. Shows often sell out, especially on weekends, so the sooner you buy your tickets, the better. The theaters are located in Old Town, which boasts a plethora of family-owned restaurants offering cuisine from around the world. For another round of pizza, go with Ranalli’s Pizza just a bit north of the theater. Cafe Ba-Ba-Reeba is a Chicago mainstay that features tapas, pinxtos, and sangria, and RJ Grunt’s serves hamburgers and other delicious, pub-style American classics. If you’re 21, grab a drink before or after the show at Old Town Alehouse, a cozy dive bar with a friendly atmosphere and kitschy art.
Grab breakfast in the dining room and then head back to your room to pack your bags. Don’t worry, you still have a full day ahead, but you’ll need to have the hostel store your bags after you check out. Join the Sunday walking tour that leaves from the second-floor information desk area. The hostel’s volunteer-led tours are a great way to see and learn about the city through the eyes of a local. You’ll get an overview of the history, architecture, arts, and culture of the city while getting one more chance to chat up other travelers.
Wicker Park is a hipster haven with locally-owned coffee shops, fancy donut places, and vegetarian eats galore. Take the Blue Line to Damen and then it’s just a few blocks to this neighborhood’s namesake park. Spend some time relaxing in the park and admiring the Victorian mansions around its borders or stroll down Milwaukee Ave., the main commercial thoroughfare. Duck into one of the many vintage shops, like Store B Vintage or Una Mae’s, or take a break at Wormhole Coffee for some of the best coffee in town.
There are a ton of great food options in Wicker Park, but we have some favorites we like to recommend. Big Star is a self-described “honky-tonk” in a defunct 1940’s gas station that offers a wide variety of tacos and chips for meat eaters and vegetarians alike. If you haven’t had your fill of pizza, try Piece, a New Haven-style pizzeria where the slices are more modest than Chicago deep dish, but just as delicious. For vegetarian, vegan, and gluten-free comfort food, head over to Handlebar. This small neighborhood joint has tasty options for everyone.
Head back to HI Chicago to grab your bags and say goodbye to your new friends and the hostel staff. Leave yourself at least an hour to get from the hostel to the airport on the L.
If you're visiting the city on a budget, take a look at a few of our favorite free things to do in Chicago.