CHICAGO RECOMMENDATIONS

By: Ely Orrego Torres

Food Recommendations

For photos and more details on my food recommendations, check out my Chicago stories on my foodie account on Instagram @saborkairos:

Part 1

Part 2

Classic Chicago Foods

  • Deep Dish Pizza: A must-try, as it’s a pie-style pizza. Try Giordano’s (meat-filled recommended) or Lou Malnati’s (great vegetarian option). Locations are spread throughout the city.
  • Chicago Hot Dog: Portillo’s is a must-visit for an authentic Chicago-style hot dog. Their beef sandwich (a juicy, flavor-packed meat sandwich) is also a local favorite. Visit the Ontario Street location for a classic Chicago atmosphere. Map
  • Chicago Beef Sandwich: Made famous by The Bear, the one featured in the show’s first season is excellent. Map
  • Garrett’s Popcorn: Order the Garrett’s Mix (caramel & cheddar). It might sound strange, but it’s delicious! It’s also a great gift, sold in decorative tins that stay fresh for weeks. Locations at Navy Pier and downtown.
  • Rainbow Ice Cream: A colorful multi-flavored cone sold at Navy Pier. Map

My Favorite Chicago Food Spots

  • FRÍO Gelato:An Argentine gelato shop with flavors like Malbec and Dulce de Leche, located in Navy Pier and Evanston.
  • BopNGrill: Korean-American fusion burgers. The kimchi burger is incredible. Map
  • Ann Sather: The ultimate brunch spot, famous for its cinnamon rolls and generous portions. Multiple locations.
  • Molly’s Cupcakes: Classic American cupcakes. Must-tries: S’mores and Crème Brûlée. Several locations.
  • Stan’s Donuts: Delicious donuts, with multiple locations around the city.
  • Forno Rosso Pizza: My favorite Neapolitan pizza in Chicago, located in Fulton Market. Try the pistachio pesto& sausage pizza. Map
  • Bonci Pizza: Another top-tier pizza spot in Fulton Market, selling by the slice and weight. Great variety! Map 
  • Casa Margarita: If you’re at Navy Pier, stop by for margaritas. They offer a tasting flight with different flavors. Map
  • Birrieria Zaragoza: One of Chicago’s best taco spots, run by a Mexican family, and even holds a Michelin star. Originally located in Archer Heights, now they have a local in Uptown. Map
  • Ramen-San Deluxe: My favorite ramen spot, with rich, flavorful broth. Lunch menu available for ~$17. Map
  • Hanabusa Café: Offers fluffy Japanese soufflé pancakes. Map
  • Sushi Rotary Bar: Conveyor belt sushi with a train that delivers custom orders. Fun experience! Map
  • The Budlong Hot Chicken: One of the best places for spicy fried chicken, inspired by Southern U.S. cuisine. Map
  • Tortello: My favorite Italian spot in Chicago, award-winning and affordable. Map
  • Raising Cane’s: My top pick for fried chicken—way better than KFC! Several locations.
  • Triple Crown Restaurant: Excellent Chinese dim sum in Chinatown. Map
  • Arepas Bien Me Sabe: Close to Millennium Park, perfect for grabbing an arepa and having a picnic. Map

What to Do in Chicago:

Tourist Attractions & Passes

If you're in tourist mode and want to visit multiple attractions/museums, it's worth getting the Chicago City Pass or Go Chicago Pass. There are various options depending on what you want to do. For example, not all passes include Shedd Aquarium, which is beautiful and highly recommended. It might be my favorite cultural spot in Chicago, though the Art Institute is also fantastic.

Walking Tours

Check out Chicago Greeter, GuruWalk, or Freetours for free, customizable walking tours based on your interests. Some focus on specific neighborhoods and provide a great introduction to the city. Chicago Greeter tours are especially great since they are led by volunteers (often retirees) who offer their time without expecting tips.

Downtown / Millennium Park: Take the Red Line subway to Lake Station, where you'll immediately see the Chicago Theatre, an iconic spot for photos, especially at night when it's lit up. Walk to Millennium Park to see the famous Cloud Gate ("The Bean") and Crown Fountain. If you have time, continue walking south along the lakefront to reach the Field Museum, Shedd Aquarium, and Adler Planetarium, an area with stunning views of the Chicago skyline.

Riverwalk: Get off at Michigan Avenue to explore the fancy shops. If you're a Starbucks fan, visit the Starbucks Reserve Roastery nearby. There's also a Garrett’s Popcorn in the area. From here, walk south to the Chicago Riverwalk, where you can grab a drink at a riverside bar. Across the river, check out Art on the Mart, a free outdoor digital art projection shown daily at evening (check times here: Art on the Mart).

Chinatown: Take the Red Line to Cermak-Chinatown Station. Walk around the neighborhood and, if you want Chicago souvenirs, this is the best place for affordable keychains, t-shirts, and magnets. Food Recommendations in Chinatown: Peking Duck: Seven Treasures; Sushi: Rotary Sushi (fun experience with a sushi train delivering your order); Dim Sum: Triple Crown; Bubble Tea: T'amo Bobba Bar, Elitea, or Uni Uni.

Shopping

If you're in shopping mode, my favorite cheap spots are Primark and Marshalls.

Top Activities

  • Architectural Boat Tour – Best at sunset. The boats depart in front of the Trump Tower on Michigan Ave., near the Apple Store. Many passes include it.
  • Lincoln Park & Zoo – Free admission, well-maintained animals. Best to visit on a nice weather day since there's a lot of walking.
  • Navy Pier: A mix of a shopping area and waterfront. In summer, they have fireworks. Good spots to grab a snack include: Frío Gelato, Rainbow Cone, Garrett’s Popcorn
  • Bahá'í Temple (Evanston): Located in Evanston near Northwestern University. Take the Purple Line to Linden Station and walk about 6 minutes. The temple is surrounded by beautiful gardens. Evanston is a wealthy area, so it's interesting to see the contrast in architecture. Home Alone fans: The McCallister house is nearby, but best reached by Uber.

Museums:

  • Field Museum – Great for natural history lovers and dinosaur exhibits 🥹❤️
  • Museum of Science and Industry – Covers a variety of topics, including WWII and U.S. imperialism.
  • Shedd Aquarium – Marine life in well-maintained environments.
  • Art Institute – Pre-Columbian, Asian, Roman, Greek, and modern art collections.
  • Museum of Contemporary Art – A smaller, cheaper alternative to the Art Institute, focusing on modern art. It’s also connected to the Art on the Mart projections.

Best Skyline Views & Panoramic Spots

  • Chicago 360° – Observation deck on the 94th floor with a thrilling glass-floor experience.
  • Skydeck Chicago – Similar to 360°, but includes a transparent glass-floor section.
  • Cindy’s Rooftop Bar – Overlooks Millennium Park.
  • Fullerton Beach – Best north-side skyline view (ideal for biking or walking).
  • Shedd Aquarium – One of my favorite south-side skyline views.

Music & Nightlife

Chicago is known for its blues and jazz bars:

  • The Green Mill – Historic jazz bar in Uptown (cash only).
  • Kingston Mines – A livelier blues venue. On weekends, Joanna Connor, a legendary blues guitarist, performs.
  • The Basement – cool music and drinks.
  • Blue Chicago –intimate and packed, so arrive early or be patient because of the crowds.
  • Buddy Guy’s Legends –historic blues club with Louisiana food.

Cool Neighborhoods

  • Pilsen – Mexican neighborhood with stunning murals.
  • Uptown – Hipster and artsy vibe.
  • Rogers Park – My old home 🥹❤️, university atmosphere, and near the beach.
  • Boystown – LGBTQ+ district near Uptown.
  • West Loop – Trendy, upscale area with great restaurants.

Getting Around Chicago:

Public Transport (Ventra Card)

  • Chicago has great metro and bus connectivity. The Red Line is the main north-south subway route. If arriving at O’Hare, the Blue Line takes you downtown.
  • Like in many U.S. cities, the subway can feel sketchy late at night or early morning. Try to avoid it at those times if possible.
  • I’m not sure of the current fare price, but you’ll need to buy a Ventra Card and load it. You can also purchase a 1-week or 3-day pass, depending on your needs.
  • The Ventra Card works for both metro and buses.

Biking

Chicago has a bike-sharing system called Divvy, available for single-use or daily passes. The Lakeshore Trail is great for biking, especially near Lincoln Park.

Uber/Lyft

  • Uber works well but is expensive (rides start at $8+ USD).
  • Lyft is usually cheaper. It also offers a "Wait and Save" option, which sometimes makes rides more affordable.
  • If coming from the airport, check Lyft’s "Wait and Save" option—it can be a cheaper alternative to other transport.
  • Use my Lyft discount code for a cheaper ride: Link

Chicago & Pop Culture

  • Batman: The Dark Knight – Chicago is Gotham City! As you walk through downtown, you'll recognize the street layouts and dark alleyways. The bank the Joker robs in the opening scene is a highlight of the Architectural Boat Tour.
  • Home Alone – The McCallister family house is in Winnetka. If you're a big fan, I recommend taking an Uber: Google Maps Link.
  • Easy (Netflix) – A fantastic series about love, heartbreak, and relationships, filmed in Chicago. Each episode is standalone, so you can watch it in any order.
  • The Bear – The Emmy-winning series takes place in Chicago. You can visit Mr. Beef, where much of the show was filmed, along with other real-life locations featured in the series.
  • Bojack Horseman – The later seasons include several animated shots of Chicago.

Recommended Itinerary

Day 1: Downtown & Riverwalk

  • Start by exploring downtown on foot. Visit the Chicago Theatre (come back at night for stunning illuminated photos).
  • Walk along the Chicago Riverwalk, passing the Trump Tower.
  • Head to Michigan Avenue for shopping and sightseeing:
  • Michael Jordan’s Steakhouse
  • Starbucks Reserve Roastery (4 floors!)
  • Fancy stores along the Magnificent Mile
  • If the weather is nice, take the Architectural Boat Tour near sunset for the best photos.
  • After the tour, catch the Art on the Mart light show.
  • For dinner, check out Ramen-San Deluxe (my favorite ramen spot).
  • Grab a snack from Garrett’s Popcorn (try the Garrett Mix).

Day 2: Chinatown & Skyline Views

  • Head to Chinatown for lunch and shopping. Souvenirs are much cheaper here!
  • Walk through the nearby Chinatown Park.
  • If you're up for more walking, take the Red Line to Roosevelt and walk towards the Shedd Aquarium for one of the best views of the Chicago skyline.
  • Continue north along the Lakefront Trail, eventually reaching Millennium Park (Cloud Gate / The Bean).
  • If this feels like too much walking, you can save part of it for Day 3.

Day 3: Lincoln Park & Lakefront Bike Ride

  • Rent a Divvy bike or take a bus to Lincoln Park.
  • Visit the Lincoln Park Zoo (free admission!).
  • Bike to Fullerton Beach for a beautiful skyline view.
  • Continue cycling along the Lakefront Trail.
  • Since this ride can be tiring, consider making it your main activity for the day.
  • September/October weather is perfect for biking, and you'll start seeing the fall colors.

Day 4: Bahá’í Temple & Uptown

  • Visit the Bahá’í Temple in Evanston (go in the morning or afternoon, depending on your schedule).
  • Head south to Uptown and explore the Vietnamese district.
  • Walk down to Boystown, a lively LGBTQ+ neighborhood.
  • In Uptown, try Birriería Zaragoza for amazing birria tacos.
  • Night option: Experience live jazz or blues at Kingston Mines or Green Mill.

Day 5: Museums & Panoramic Views

  • Dedicate the day to museums and/or panoramic city views.
  • Field Museum (dinosaurs & natural history)
  • Shedd Aquarium (marine life)
  • Art Institute (classic & modern art)
  • Museum of Science & Industry (interactive exhibits)
  • Museum of Contemporary Art (modern & contemporary pieces)
  • For breathtaking city views, visit either:
  • Skydeck Chicago (with the famous glass ledge)
  • 360 Chicago Observation Deck (with Tilt, a thrilling glass-floor experience)