The ultimate road trip guide to Chicago

Best tourist attractions in Chicago 

The Windy City offers incomparable sights and adventures to any road traveler. Some of the most popular tourist attractions in Chicago to check out are:
Getting around in Chicago with car rental or airport shuttle 

A road trip does not necessarily mean you're driving your own car. You may be out for a business travel and need a car rental. In Chicago, you can get plenty of car rental deals from, Alamo, Thrifty, Enterprise, and Avis.

Find great rates on great vehicles at

Top things to do in Chicago 

If there's one thing Chicago is not, that's the word boring. You will never run out of things to do in the Windy City. So gear up and visit any of these places while you're traveling:

  Chicago Destination Page
  • Chicago Planet Food Tours 
  • Chicago Architecture Foundation 
  • Seadog Cruises  
  • Signature Lounge 
  • UP Comedy Club 
  • Second City 
  • American Girl Place 
  • Christkindl Market 
  • Merchandise Mart 
  • Chicago Shakespeare Theater 
Indulge in instant gratification and save up to 90% on the best local restaurants, shops, events and more at!

Road chow: Where to eat in Chicago

Are you looking for affordable and family-friendly restaurants in Chicago? I've listed some of my favorites. They never disappoint!
  • Birchwood Kitchen 
  • HB Restaurant  
  • Sapori Trattoria 
  • Longman & Eagle 
  • Xoco 
  • Davanti Enoteca 
  • The Purple Pig 
  • Hopleaf Bar 
  • Smoque BBQ 
  • Au Cheval 
Find Today's Daily Deal on the Best in Chicago!

Best venues in Chicago for upcoming events 

Chicago is home to the best sports venues and theater in the U.S. When you're on a road trip, make it a point to check out an arena or a football field.
  • Wrigley Field 
  • US Cellular Field 
  • Chicago Theatre 
  • Cadillac Palace 
  • Allstate Arena 
  • United Center 
  • Skyline Stage at Navy Pier 
  • Bank of America Theater 
  • House of Blues 
  • Ford Center for Performing Arts 
Shows are just as popular, with mainstays like The Blue Man Group and The Book of Mormon.


Travel essentials for your Chicago road trip 

Plans available through Travel Guard can provide you with coverage for unexpected medical expenses while on a trip. There's nothing more frustrating than finding out you left something at home or your luggage was missing. Packing for your trip to Chicago is one of the most important things in your checklist. Find everything travel and travel accessories at RoadTripConnect.

Book a hotel in Chicago 

Traveling with a Group? Confirmed Online Reservations Worldwide. Book Now!

Chicago's top hotels are just waiting around the corner, with tons of deals being offered online. Which one is your pick? Whether you're out for a swanky stay or a simple getaway, check out the best hotels at the best price:

  • Palomar Chicago 
  • Four Seasons Hotel Chicago 
  • The Talbott Hotel 
  • Park Hyatt Chicago 
  • Conrad Chicago 
  • Radisson Blu Aqua Hotel 
  • Carlton Inn Midway 
  • The James Chicago Hampton Inn & Suites Downtown 
  • Days Inn Chicago
Find the Best Chicago Hotel - Search over 30 Hotel Sites Now

Flying to Chicago?

If you're flying to Chicago instead of driving, your best bet is to find the cheapest flight tickets online through various flight booking sites such as Travelocity, Expedia or Cheapoair.

Book Cheap Air tickets with CheapOair & Save Big on Travel.
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About the Author

The Editor
We like the freedom of open road travel. Whether it's in the streets of London to the outback of Australia, nothing beats driving your vehicle and enjoying your trip -- your way. Join us in sharing ideas on where to go, where to stay, and fun things to do on roadtrip stopovers all over the world.

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