Chicago isn’t just about world-class attractions — it’s also a city full of iconic eats, memorable hotels, and neighborhoods worth exploring. Here’s your guide to enjoying the best food, finding a great place to stay, and maximizing the best experiences in Chicago.
Iconic Eats
1. Rainbow Cone
Easily, one of the best experiences in Chicago is sampling a Rainbow Cone. This multi-flavored ice cream treat layers chocolate, strawberry, Palmer House (New York cherry, pineapple, and walnut), pistachio, and orange sherbet — a sweet tradition since 1926 — and man, is it good. This beauty runs around $7-$8.
2. Gene & Georgetti
For a classic Chicago steakhouse, head to Gene & Georgetti. Known for its perfectly cooked steaks, Tuscan Italian-inspired sides, and old-school charm, it’s a must for carnivores and foodies alike. You can’t go wrong with a classic Caesar salad, and a homemade pasta dish is a must.
3. Chicago-Style Pizza & More
While deep-dish pizza gets the headlines, don’t overlook the city’s other culinary gems. From Chicago-style hot dogs to Italian beef sandwiches, there’s something for every palate. I discovered some of my favorite eats at a French counter-service spot.
Hotel Stays
The Hilton Chicago Hotel
Located right on Michigan Avenue with stunning views of Grant Park and Lake Michigan, The Hilton Chicago is a fantastic home base for exploring downtown. With its central location, it’s perfect for first-time visitors who want easy access to shopping, museums, and nightlife.
The hotel offers plenty of space to unwind, with 1,544 rooms and suites designed for comfort and convenience.
DoubleTree by Hilton Hotel Chicago O’Hare Airport – Rosemont
Looking for a lower price tag without sacrificing quality? The DoubleTree by Hilton Hotel Chicago O’Hare Airport – Rosemont offers fantastic rooms, a convenient location near Parkway Bank Park Entertainment District and Rivers Casino Des Plaines. Plus, it has easy access to O’Hare Airport.
More Things to Play
Shop the Magnificent Mile
If shopping, dining, and sightseeing are on your itinerary, the Magnificent Mile will be one of the best experiences in Chicago. This bustling stretch of Michigan Avenue runs from the Chicago River up to Oak Street and offers more than 460 shops, restaurants, and attractions.
Whether you’re splurging on luxury brands like Gucci and Burberry or pop into more budget-friendly department stores, you’ll find endless options along this world-famous avenue. Magnificent Mile is also home to some of Chicago’s most iconic landmarks, the Wrigley Building and the Chicago Water Tower, one of the city’s few surviving structures from the Great Fire.
Fun Fact: The official eastern starting point of Route 66 is at the intersection of Adams Street and Michigan Avenue in downtown Chicago. It’s not directly on Magnificent Mile, but very close.
Navy Pier
Navy Pier is one of Chicago’s most iconic destinations, stretching along Lake Michigan and open year-round. This historic pier blends attractions, fun dining spots, shopping, and entertainment, making it a perfect stop for families, couples, or solo travelers.
Don’t miss a ride on the Centennial Wheel for stunning city views, explore Pier Park’s rides, or catch a show at the Chicago Shakespeare Theater. Seasonal events, dining cruises, and epic summer fireworks make Navy Pier a lively, must-see spot in the heart of the city.
Big Bus Tours
A hop-on-hop-off tour with Big Bus Tours is ideal for covering the city efficiently, connecting neighborhoods, and seeing highlights like the Museum Campus (for Field Museum and Shedd Aquarium), Skydeck Chicago & Willis Tower, and Millennium Park & The Art Institute of ChicagoGrant Park.
Don’t forget to check out our guide to Chicago attractions to plan the full itinerary.
Tips to Save
Chicago CityPASS is the easiest way to save on top attractions (and often you can reserve your timed spot for faster entrance). With one purchase, you can enjoy discounted access to the Skydeck Chicago and Shedd Aquarium (plus a 4-D Experience), plus your choice of 3 other attractions, including:
- Field Museum
- Griffin Museum of Science and Industry
- 360 CHICAGO Observation Deck and more.
Whether it’s eating, staying, or exploring, Chicago offers an unbeatable combination of attractions, food, and history. Plan wisely, and your trip will be unforgettable.
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