Chicago City Sightseeing Tours

Chicago City Tours familiarize you with major landmarks and are an excellent way to see Chicago in a short period of time. Choose from Trolleys, Open Top Bus and Guided Motorcoach Tours. more

COMBO: Tours combined with popular activities

Shopping, Antiques, Wines and More

• Shopping Excursion to the Chicago Premium Outlets in Aurora, IL
• Guided Shopping Tours of Chicago - Shop Urban Chicago!

Chicago Adventure Tours and Activities

• Chicago Helicopter Tours 30 to 90 minute Sightseeing Flights
• Chicago Area Hot Air Balloon Flights Sunrise and Sunset Flights

Also see Haunted, Bike and Hike and Segway Tours listed below.

Chicago Area Architecture Tours

Learn about the history, folklore, culture and food of Chicago's distinct neighborhoods and architecture. Additional day tours available of the surrounding cities and towns.

• Chicago The White City - The 1893 Columbian Exposition Tour
• Chicago Architecture Foundation Segway Tour

Chicago Bike and Hike Tours

On these Bike and Hike tours, you'll cover more ground than bus tours while discovering the pulse of the city ."Top 5 things to do in Chicago!" - MSN and CitySearch.com Come join in the fun -- we'll be the highlight of your trip!

Chicago Walking Tours

Select from Day or Evening - Theater, History, Architecture, Culinary, Shopping or Adventure walking explorations.

Activities and Adventures

Air, Land and Sea Tours and Adventure Activities by Seadog Speedboat, Airplane, Helicopter, Hot Air Balloon and more. All Seadog Cruises

Chicago Ghost Tours

Chicago Haunting's Tours offer the visitor a wide array of professional authors and ghost researchers to present the "other side" of Chicago History!

Gangster Dinner Show or Noble Horse Theatre Shows

At Tommy Guns Garage and Dinner Show join da dolls for non stop comedy & dangerous fun! Noble Horse Theatre presents spectacular horse productions in a historic 19th century riding hall.

Chicago Segway Tours

Riding your very own Segway will forever change the way you see and remember Chicago, as it is more intimate than a bus or driving tour and allows you to cover much more ground than any walking tour.

• Chicago Guided Lakefront Segway Tour
• Chicago Northern Adventure Guided Segway Tour
• Chicago Glide at Night Guided Segway Tour

Featured Sightseeing Tour and Boat Cruise Companies in Chicago

Shop these premier sightseeing, vacation, activity, and cruise companies to make the most of your vacation. Tour Chicago with these handpicked "best of the best" tour operators.

Dining Cruise Companies at Navy Pier

Chicago Dining Cruises

Enjoy a two or three-hour escape on board these luxury cruising vessels. Each voyage has culinary treats, music and spectacular Chicago skyline views. Lunch, brunch, dinner & fireworks cruises.

Lunch and Afternoon Cruises

Chicago Brunch Cruises

Dinner and Dancing Cruises

Chicago Blues Tours

From the Deep South to the city that made the Blues famous, you know the names, the places and the faces. So what could be more exciting than actually traveling the path of some of the most famous blues masters of all time?

Chicago Sightseeing Boats

Sit back, relax and enjoy boat cruises in and around Chicago and past the city skyline. See the Lake Michigan waterfront and the Chicago River.

Summer Fireworks Activities

Navy Pier puts on a spectacular fireworks display every Wednesday at 9:30 p.m. and Saturday at 10:15 p.m. from Memorial Day thru Labor Day Weekend (weather permitting). Enjoy the show with these fun tours and activities.

Go Chicago Card

Go Chicago Card Save on your Chicago vacation. Get unlimited FREE general admission to over 25 attractions and tours for one low price, and discounts at some of Chicago's top retailers and restaurants!

CityPass Chicago

Visit Five Chicago Attractions.... for one low price! Good for Nine Days. Tour and explore at your own pace.

Sailing Cruises and Kayak Trips

Lake Michigan sailing and Chicago kayaking are both within your reach on your next trip to the Windy City. Make reservations in advance. Sailing or Kayak

Chicago Museum Tours

Our Museum Tours bring you to the top Art Museums, Aquariums, Train Museums, Planetariums and Botanical Gardens in and around Chicago.

• Gray Line City North Shore Tour combined with the Chicago Botanic Gardens
• Gray Line City South Shore Tour combined with the Art Institute Treasures
• Chicago City Pass Includes, The Art Institute of Chicago, Field Museum, Shedd Aquarium, Adler Planetarium & Astronomy Museum and Museum of Science and Industry.

Attractions, Shows and Multi-Day Tickets

Chicago and Chicagoland Attraction and Show Tickets. Great for individuals, couples, groups and families looking for some fun for all ages. Try the multi-day attraction and museum passes to save money and time.

Chicago Hotel Reservations

Book Chicago Hotel Reservations ....Stay near Michigan Avenue, The Loop, Lakefront, O'Hare or Midway Airport Areas. Save up to 65%!

Chicago Vehicle and Boat Charters

Solutions for all transportation needs. Charter Vehicles Jeeps, SUV's Motorized Trolleys, Limousines, Yachts, Sailboats and Motor Coaches. Charters, Shuttles, Tours and Transfers.

• Motorized Trolley or Double Decker Bus Charter a Trolley for your next Event
• Sailing Charters Fun 1 Day and Overnight Sailing Charters

Restaurant Reservations

Book lunch or dinner reservations at top Chicago Restaurants. Instant confirmation for hard to get tables!