Chicago

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JunSummer

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Chicago
Breakfast

$$$

Tea

140 E Walton Pl, Chicago

Google Map Location

The Drake is a Chicago hotel that stands apart with a legacy of legendary acclaim. Offering historic dining experiences, picturesque Lake Michigan views, and convenient access to the charming Gold Coast neighborhood, it’s a destination like no other in the city.

Chicago
Breakfast

$$

Cafe

502 E Illinois St, Chicago

Google Map Location

Kanela, which translates to ‘Cinnamon’ in Greek, has earned the prestigious title of “Best Breakfast in Chicago” by USA Today. It’s become synonymous with delivering the finest breakfast experiences in the Windy City.

Chicago
Breakfast

$$

American

1746 N Wells St, Chicago

Google Map Location

Discover a family-owned, local chain of casual American restaurants that takes pride in offering an extensive menu featuring all-day breakfast options alongside a diverse selection of delicious dishes.

Blog

Crewfare Travel

Events & Tours

Top 10 NFL Tailgates Worth Traveling For 🏈

There’s going to an NFL game, and then there’s traveling for the full game-day experience. The best football cities turn Sunday into an all-weekend event, with packed parking lots, legendary food, die-hard fan traditions and pregame parties that are almost as memorable as the game itself. Whether you’re planning an away-game trip or just looking for an excuse to experience a new city this football season, these are 10 NFL tailgates worth traveling for plus where to stay with Crewfare...

Crewfare Travel

Concert

Crewfare Partners with Sueños Music Festival to Support Community-Driven Festival Travel

Crewfare Travel

Travel

Best Cities for Festival and Food Scenes

Crewfare Travel

News

The Ultimate Guide to Chicago’s Holiday Season: 12 Festive Things to Do in the Windy City

Chicago has a way of surprising people who think they already know it. Whether you're visiting for a conference, a game day, a festival, or just a long weekend by the lake, the Windy City delivers a mix of world-class culture, deep-dish debates, and neighborhood charm that's hard to match. This guide covers the top things to do in Chicago, from wandering the galleries of the Art Institute of Chicago to strolling the historic quads of the University of Chicago in Hyde Park. Along the way, you'll find some of the best ways to see the city without spending a dime, including Chicago's excellent free walking tours through downtown and the Loop, plus recommendations for the best restaurant experiences, from a growing list of Michelin-recognized kitchens to classic deep-dish spots and lakefront hot dog stands. Spend your days biking the Lakefront Trail, catching the skyline from Millennium Park, or people-watching on Michigan Avenue, then experience Chicago's famous nightlife with rooftop bars, blues clubs, and live jazz. Whether it's your first visit or your fifth, Chicago offers something for every traveler, making it one of the Midwest's most exciting destinations to explore.

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