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Looking for a Flight to Chicago?
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Activities in Chicago
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City Trip to Chicago: Top Attractions, Deals, and Tips
Chicago also referred to as the "Windy City." Nestled on the shores of Lake Michigan, Chicago is a city of stunning architecture, rich history, and diverse culture. Whether you're a foodie eager to sample world-renowned cuisine such as the deep dish pizza, an art enthusiast ready to explore some of the country's finest museums, or an adventurer looking to experience the lively neighborhoods, Chicago has something for everyone.
This comprehensive guide is designed to help you make the most of your visit. From iconic attractions like Millennium Park and the Willis Tower Skydeck to hidden gems in the city's eclectic neighborhoods, we provide detailed insights and tips to ensure your trip is unforgettable, as well as, the best deals on flights and hotels to make for the ultimate city trip in this iconic US city.
Top Attractions in Chicago
Navy Pier
One of Chicago's most iconic and popular spots, Navy Pier draws in millions of visitors each year. On the shores of Lake Michigan, this 3,300-foot-long pier offers tons of entertainment, delicious food options, and plenty of shops to explore. Here, you'll also find the Centennial Wheel, which is a giant ferris wheel that offers incredible views of the Chicago skyline. You'll also find Pier Park which is an amusement park that is fun for all ages. Finally, this is the spot to grab a boat tour around Chicago.
Millennium Park
Millennium Park is located in the heart of Chicago, spanning 24.5 acres. The park is a major cultural hub and a vibrant public space that attracts millions of visitors. Here, you'll find the famous "The Bean" sculpture, the crown fountain, and the concert venue; Jay Pritzker Pavilion.
Willis Tower Skydeck
What was formerly known as Sears Tower, the Willis Tower Skydeck is an iconic skyscraper in Chicago and offers a clear observation deck. It is 1,452 feet high and was once the tallest building in the world.
The Art Institute of Chicago
One of the oldest art museums in the US, The Art Institute of Chicago was founded in 1879 and houses iconic pieces of art such as, "Water Lilies" by Claude Monet, "American Gothic" by Grant Wood, and "The Bedroom" by Vincent van Gogh.
Neighborhoods to Explore
The Loop: Grant Park, shopping, and theaters
River North: art galleries, nightlife, and great dining
Lincoln Park: Lincoln Park Zoo, conservatory, and parks
Wicker Park/Bucktown: boutiques, restaurants, and street art
Hyde Park: University of Chicago, Museum of Science and Industry
What to Eat in Chicago: Iconic Chicago Food
Deep-dish pizza
Restaurants to try it at:
Lou Malnati’s Pizzeria
Giordano’s
Gino’s East
Chicago-style hot dogs
Restaurants to try it at:
Portillo’s
Superdawg Drive-In
Gene & Jude’s
Italian beef sandwiches
Restaurants to try it at:
Al’s Beef
Mr. Beef
Portillo’s
Chicago Donut
Restaurants to try it at:
Dat Donut
Do-Rite Donuts
Stan’s Donuts & Coffee
Pirate Tip: Visit Bavettes steakhouse, or Girl & The Goat - two of the most celebrated restaurants in Chicago, and you can grab a seat at the bar without the difficult-to-get reservations, and still try the full food menu.
Bars and Breweries:
The Aviary
Revolution Brewing
Green Mill Cocktail Lounge
The Comedy Bar - The name says it all
Green Mill - Al Capone's ex-haunt
Kingston Mines - awesome live blues venue; resident band is Johanna Connor who went viral thanks to some ridiculous guitar playing
Go far enoug north and visit Hopleaf - great for beer afficionados
Accommodation Options in Chicago
Below, we've provided our suggestions for great hotel options based on your budget. Whether you're looking for a luxury 5-star hotel, a mid-range 3 to 4-star hotel option, or budget accommodations/hostel, we've provided our recommendations below.
Luxury Hotels:
The Peninsula Chicago: Usual rates are $500 - $1,000+
Four Seasons Hotel Chicago: Usual rates are $500 - $1,000+
Waldorf Astoria Chicago: Usual rates are $500 - $1,000+
The St. Regis Chicago: Usual rates are $500 - $1,000+
The Langham, Chicago: Usual rates are $550 - $1,000+
Mid-Range Hotels
Hotel Lincoln: Usual rates $110 - $250+
AC Hotel by Marriott Chicago Downtown: Usual rates $140 - $300+
The Godfrey Hotel Chicago: Usual rates $130 - $300+
LondonHouse Chicago: Usual rates $120 - $250+
The Drake: Usual rates $150 - $300
Budget Options
HI Chicago Hostel: Usual rates $30 - $80
Freehand Chicago: Usual rates $20 - $50
Wrigley Hostel: Usual rates $35 - $50