Chicago Trips and Itineraries



Adventure Chicago: Experience a summer Saturday in the Windy City

An action-packed Saturday full of Chicago sun and sights.

Category: Active/Adventure

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Nile Local Expert: Meghann

Best breakfast spots in Chicago

10 restaurants with Chicago's best breakfast

Category: Best of...

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Nile Local Expert: Meghann

Best budget picks in Chicago

Ten of Chicago's best picks for the traveler on a budget

Category: Best of...

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Nile Local Expert: Meghann

Best Chicago nightlife

The best places to create memorable Chicago nights

Category: Best of...

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Nile Local Expert: Meghann

Best Chicago restaurants

The top 10 places to dine, nosh, and gorge in Chicago

Category: Best of...

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Nile Local Expert: Meghann

Best live music venues in Chicago

The top 10 places to hear live tunes in the Chi

Category: Best of...

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Nile Local Expert: Meghann

Best performance spaces in Chicago

The top places to see live theater and dance in Chicago

Category: Best of...

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Nile Local Expert: Meghann

Chicago's Best Late Night Eats

Where to eat in the wee hours of the morning...

Category: Best of...

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Nile Local Expert: Adi

Romantic Chicago: Keep each other cozy in the Windy City

A day of relaxed activities with a focus on warmth and one-on-one time.

Category: Romantic

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Nile Local Expert: Meghann

The best free finds in Chicago

Experience Chicago's finest without spending a dime

Category: Best of...

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Nile Local Expert: Meghann

The best lodging in Chicago

10 of Chicago's top spots to hang your hat

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Nile Local Expert: Meghann

Top 10 hidden gems in Chicago

10 of Chicago's greatest secret spots

Category: Best of...

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Nile Local Expert: Meghann

Top 10 things to do in the Chicago summer

Summer in the city: the must-do list for fun in Chicago's sun

Category: Best of...

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Nile Local Expert: Meghann

Hip Chicago: A weekend in Wicker Park

Two days bopping around in one of Chicago's hippest hoods.

Category: Cool and Hip

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Nile Local Expert: Meghann

Weekend in Chicago: Chicago in two days - The Ultimate Weekend

A short but sweet taste of Chicago

Categories: Best of..., First time visit

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Nile Local Expert: Adi

Favorite Kid-Friendly Activities in Chicago

Ciao Bambino's favorite activities with kids in Chicago

Category: Kid Friendly

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Partner: Ciao Bambino!

Kid-friendly Chicago: Family fun in Chi-Town

Three days, packed with Chicago activities that will delight the entire family.

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Nile Local Expert: Meghann

Your First Time in Chicago

The Must-Sees, Must-Eats, and Local Recommendations

Categories: Arts and Culture, Best of..., First time visit

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Nile Local Expert: Adi

Off the beaten path Chicago: Travel like a local in Chicago's north side neighborhoods

Spend seven days immersed in the local flavor of Chicago's northern nieghborhoods.

Category: Off the Beaten Path

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Nile Local Expert: Meghann

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