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Our Best Deals for a Trip 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