Comprehensive Guide to Chicago

Group 6 Chicago, IL
Spring, Summer, Fall, Winter
$, $$, $$$

About the location

Come eat, drink, and be merry in America's Second City! Chicago is a top food, entertainment, and hospitality destination that is sure to please all types of travelers, from families with kids to a couple escaping for a romantic getaway. Use this guide to plan for any length of stay but if you're looking for a suggested timeline, I'd say 2-4 days will give you a good taste of what this Midwestern metropolis has to offer. I've lived in Chicago for the past five and a half years and learned a thing or two about how best to have a good time in this amazing city. I hope you come and enjoy Chicago as much as I do!

Guide Highlights

Top food and drink recommendations

Eat your way through the hottest restaurants, local eats, and Chicago classics in one of the top foodie destinations in the world!

A list of attractions to enjoy during all four seasons

Find attractions listed by interest and season, as well as tips for looking up local events happening in every neighborhood!

Guide Summary

This guide serves as a comprehensive tool to plan a trip suited to your budget and interests. I recommend Chicago as a romantic getaway or guys/girls weekend destination but you'll find plenty of family friendly options in this guide! 

  • Best areas to stay in Chicago
  • Where to eat and drink during your trip
  • Where to catch live music or a show
  • Variety of options of every budget and interests
  • Tips for making the most of your stay

Featured in this guide

Local food
Group 31 Museums
Foodie favorites
Laid-back or relaxation
Group 38 Bike-friendly
Group 33 Walkable
Group 13 Public transportation

Great for these trips

Family with kids
Girls / Guys Trip
Family without kids
Romantic / Honeymoon
Weekend Getaway


This guide has not been reviewed yet.

  • Guide Architect

    Madeline Seghers

    Madeline Seghers

    Northwest gal, currently Midwest livin'. I've been to 20 countries and counting! You can find me always plotting my next great adventure.

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