For convenience, the following suggestions are located near the recommended sites (River North and The Loop neighborhoods). With any place in Chicago, we recommend booking reservations in advance.

- Beatnik on the River: A beautiful Mediterranean-inspired restaurant along on the river known for their brunch, but their entire menu is delicious. We love this place. Our favorite menu items are baba ganoush, fried rice, mezze board, shakshuka, and tuna crudo.

Located in: The Loop

- Francois Frankie: A charming French restaurant featuring a carousel bar. We like the oysters, steak tartare, braised short rib dip, and steak diane.

Located in: The Loop

- Broken English Taco Pub: A casual Mexican street-style taco joint with murals, eclectic music, and a lively atmosphere. All the tacos are good and make sure to get an order of their guacamole.

Located in: The Loop

- Barrio: A modern, upscale Mexican restaurant offering dishes like a taco tower, enchiladas, and fajitas.

Located in: River North

- Gilt Bar: An upscale, moody restaurant serving elevated American comfort food and classic cocktails in a speakeasy-style ambiance. We recommend their truffle bucatini, tenderloin steak tartare, prime rib French dip, and cheeseburger. The downstairs features a photobooth and you put one of the photo copies onto the hallway with the others.

Located in: River North

- Bavettes Bar & Boeuf: A French-inspired steakhouse in a moody, speakeasy ambiance known for their steak, seafood, and sides. You will especially need to book reservations at least a few weeks in advance; it's difficult to get in, but it's worth it if you can.

Located in: River North

- Siena Tavern: An Italian restaurant. We like the grilled octopus, shaved brussel sprouts, and squid ink linguine.

Located in: River North

- Avec: A Mediterranean-inspired restaurant. We like the small plates and pasta dishes.

Located in: River North

- Sushi Nova: A solid all-you-can-eat sushi restaurant, right around the corner from where we live, with affordable sushi and a la carte options.

Located in: The Loop

- Ramen-San: Our favorite ramen in town. We recommend the chicken and vegetable gyoza and the 10 hour tonkotsu ramen.

Located in: River North

- Firecakes: A donut shop known for its small-batch, handcrafted treats made fresh daily, offering a variety of classic and inventive flavors like the butterscotch praline and Valrhona chocolate iced.

Located in: River North

- Dessert Dealer: A dessert counter located within Parlor Pizza Bar's Chicago locations, offering large dessert tacos.

Located in: River North

SPECIAL CHICAGO STAPLES

- Magnolia Bakery: Classic American baked goods, and famous for their banana pudding - definitely a must-try!

Located in: The Loop

- Portillo's: A fast-casual restaurant chain, renowned for its iconic Chicago-style hot dogs, Italian beef sandwiches, char-grilled burgers, cheese fries, and decadent chocolate cake shakes, all served in a nostalgic, Prohibition-era-themed setting.

Located in: River North

- Parlor: Rayce's favorite Neapolitan style pizza in town in a casual and cute place.

- Lou Malnati's: One of Chicago's deep dish casual restaurants. Their main competitor is Giordano's but we like Lou Malnati's better. Technically, our favorite deep dish place in town is Pequod's but it's further away/inconvenient to get.

Located in: River North

- Robert's Pizza and Dough Company: A great option for New York style pizza/wood-fire oven. And, it's near the water on the Ogden Slip, which feeds into the Chicago river.

Located in: River North

We have been to all of these below sites and loved them all.

- Chicago Riverwalk: It's a beautiful walk right by the water with places to stop for a drink, coffee, or food along the way. You can take it all the way east to the lake and connect to the lakefront trail. Jessica and Rayce live a block away from the west end of the riverwalk.

- Lakefront Trail: You can walk for miles north and south on the lakefront trail seeing both city and the boats on the water.

- Millennium Park & The Bean: Walk around the park seeing the monuments, art installations, The Bean, and walk the bridge over to Maggie Daley Park.

- Buckingham Fountain: Within Grant Park, it's one of the largest fountains in the world. You can walk through the park and also see the lake as the fountain is right near the lake. At night, there are light and water shows every 15 mins.

- Navy Pier: Walk along the pier for a view of the lake and the skyline behind you. It also includes various entertainment, dining, shopping, and cultural attractions. Highlights include the iconic Centennial Wheel, the Chicago Children's Museum, theaters, and seasonal events.

- Architecture Boat Tour: Take a scenic cruise along the Chicago River, learning about the city’s rich architectural history. The tour highlights iconic buildings and landmarks, offering insights into the styles and stories behind Chicago’s skyline. It’s both relaxing and educational - this is the top attraction locals enjoy as well. Learn more here and here.

- Magnificent Mile: It's the spot for upscale shopping. This is also where you can get a cup of coffee at the Starbucks Reserve Roastery, the largest Starbucks in the world.

- The Ledge at Skydeck: Located on the 103rd floor of the Willis Tower (formerly the Sears Tower), you can see a breathtaking view of Chicago from 1,353 feet above ground. It's the highest observation deck in the United States - you can see across four states on clear days. A standout feature is The Ledge - glass boxes that extend 4.3 feet from the building, so you can step out and look straight down at the city below. It also includes an immersive museum showcasing Chicago's rich history and architecture.

- 360 Chicago: ​It's an observation deck located on the 94th floor of the John Hancock Center. At 1,030 feet above street level, it offers panoramic views of Chicago's skyline, Lake Michigan, and, on clear days, parts of four states. The observation deck also includes CloudBar, a cocktail lounge offering local craft beverages and light snacks. And, there are also interactive exhibits about Chicago's history and neighborhoods.

- TILT: It's an enclosed moving platform that tilts visitors outward from John Hancock Center building to a 30-degree angle, providing a unique downward-facing view of the city.

SOME OF THE TOP MUSEUMS

- Art Institute of Chicago: Founded in 1879, it's one of the oldest and largest art museums in the United States. It's across the street from Millennium Park. It houses a collection of over 300,000 works spanning 5,000 years of human talent. It's renowned for its extensive collections of Impressionist and Post-Impressionist paintings, including masterpieces like Georges Seurat's A Sunday on La Grande Jatte, Grant Wood's American Gothic, and Edward Hopper's Nighthawks.

Museum Campus:

- Field Natural History Museum: It houses over 24 million specimens and artifacts, offering exhibits like "Inside Ancient Egypt," featuring mummies and a reconstructed tomb, and "The Ancient Americas," which showcases 13,000 years of human history. Notable displays include SUE, the most complete Tyrannosaurus rex fossil discovered, and Máximo the Titanosaur, the largest dinosaur ever exhibited.

- Shedd Aquarium: It's one of the world’s largest and most renowned indoor aquariums housing over 32,000 animals representing around 1,500 species, including fish, marine mammals, birds, reptiles, and amphibians. Exhibits include "Amazon Rising," "Wild Reef," and the "Abbott Oceanarium," which features beluga whales and Pacific white-sided dolphins.

- Adler Planetarium: The museum features three state-of-the-art domed theaters, including the Grainger Sky Theater, offering immersive sky shows. Exhibits include "Mission Moon" and "The Universe: A Walk Through Space and Time". It also houses the Doane Observatory, Chicago's only public research-active observatory, enabling visitors to observe celestial objects through a large aperture telescope.

- Le Chocolat du Bouchard: This is a perfect place if you want a sweet treat, whether it's a sweet dessert or dessert beverage (cocktail or hot chocolate). You can pick something out from their large display at their counter or order off their menu. We enjoyed this spot.

- Buona: If you're looking for a quick bite to eat and you're interested in a local Chicago related classic, grab an Italian beef sandwich from this place. This is our favorite Italian beef place, and it worked out that they have a location in Naperville.

- Portillo's: Mentioned above in the Chicago section as well. If you're looking for a quick bit to eat and you're interested in a local Chicago related classic, try a Chicago hot dog from here. Their Italian beef sandwich isn't bad here, but Buona is better for that.

- Old Town Pour House: This is a solid casual American restaurant with a variety of options.

- Cooper's Hawk Winery & Restaurants: This is a bit nicer dinner spot with a variety of options. And, as you can guess, they also have an extensive wine list.

- Downtown Naperville & Riverwalk: It's a cute area to walk around and see the various shops, restaurants, and bars. They're all right near the riverwalk so it's convenient to then have a nice walk by the water. Here's a map of the various establishments. If you got a rental car and are driving, here's a handy parking map. We really enjoyed this whole area - it's very cute.

- Riverwalk Park: If you're just wanting to go for a walk by the river, venture here for some trails and art pieces along the way.

- Millennium Carillon: It's a 160-foot-tall bell tower located in Moser Tower at the base of Rotary Hill along the Riverwalk. It houses a 72-bell musical instrument, making it one of only four Grand Carillons in the world. You can climb 253 steps to the observation deck and see views of Naperville, and on clear days, the Chicago skyline. Guided tours are $3 per person for ages 5 and older; children 4 and under are free.