Best North America Tours from Chicago

North America Countries Overview

Technically, North America includes 23 countries, but for most travelers, three stand out as the biggest players:

United States: The U.S. is a traveler’s playground, offering everything from the skyscrapers of New York and Los Angeles to natural wonders like the Grand Canyon, Yellowstone, and the Florida Keys. It’s also a hub for road trips - whether along Route 66 or the Pacific Coast Highway.

Canada: Known for its vast landscapes, friendly locals, and diverse cities. From the Rockies in Alberta to Toronto’s cultural mix and Quebec’s European charm, Canada blends wilderness with cosmopolitan life. It’s also a top spot for skiing, hiking, and wildlife watching.

Mexico: A country where history, food, and nature meet. Explore ancient ruins like Chichen Itza, indulge in world-renowned cuisine, and relax on the beaches of Cancun or Tulum. Mexico also offers unique experiences like cenote swimming and Day of the Dead celebrations.

Other highlights in the region include the Caribbean islands, Belize, Costa Rica, and Guatemala, each offering tropical vibes and rich culture worth adding to a broader itinerary.

Top Destinations in North America

United States

New York City: Iconic attractions include the Statue of Liberty, Empire State Building, and Central Park. Beyond sightseeing, explore Brooklyn’s food scene and diverse neighborhoods.

Grand Canyon: One of the most visited natural wonders of the world. Hiking the South Rim or rafting the Colorado River are unforgettable ways to experience it.

San Francisco: Known for the Golden Gate Bridge, Alcatraz Island, and vibrant neighborhoods like Chinatown and the Mission District.

Orlando: Theme park capital of the world, home to Walt Disney World and Universal Studios.

Canada

Banff & Lake Louise: A postcard setting with turquoise lakes and snow-capped peaks. Hiking, canoeing, and winter skiing are year-round options.

Toronto: Canada’s largest city offers a skyline punctuated by the CN Tower, a thriving arts scene, and easy access to Niagara Falls.

Montreal & Quebec City: Centers of French heritage, famous for cobblestone streets, Gothic churches, and unique gastronomy (poutine, anyone?).

Vancouver: A west coast gem with beaches, mountains, and a lively multicultural food culture.

Mexico

Cancun & Riviera Maya: White-sand beaches, Mayan ruins like Tulum, and world-class diving in Cozumel.

Mexico City: A blend of ancient Aztec history and modern vibrancy. Don’t miss the Zócalo, Frida Kahlo Museum, and nearby Teotihuacán pyramids.

Oaxaca: Known for its colorful festivals, mezcal distilleries, and traditional cuisine.

Copper Canyon: Larger and deeper than the Grand Canyon, best explored by train on the Chihuahua al Pacífico railway.

For curated trip ideas, check out North America vacation packages that combine these highlights into practical journeys.

Best Time to Visit North America

Because the continent spans multiple climates, the best time to visit depends on where you’re headed. Summer (June-August) is ideal for national parks in the U.S. and Canada, though it can be crowded.

Fall (September-October) is perfect for New England’s foliage and wine country harvests. Winter (December-February) brings ski season in the Rockies and Whistler, while Mexico offers warm beaches. Spring (March-May) is excellent for cherry blossoms in Washington, D.C., and festivals in Mexico like Semana Santa.

How to Get Around North America

North America is huge, so how you travel depends on your itinerary:

Flights: With vast distances between cities, domestic flights are often the fastest way to travel, especially in the U.S. and Canada.

Road Trips: Driving is a classic North American travel style. Routes like California’s Highway 1, the Canadian Rockies Parkway, and Mexico’s Yucatán Peninsula loop are popular choices.

Trains & Buses: Amtrak in the U.S. and VIA Rail in Canada cover scenic routes, while Greyhound and regional buses connect smaller towns. Mexico also has reliable long-distance bus services.

Public Transport: Major cities like New York, Toronto, and Mexico City have extensive subway and bus networks that make exploring easy without a car.

Sample North America Travel Itineraries

1-Week Itinerary: East Coast USA

Day 1-2: New York City - Explore Times Square, Central Park, museums, and Broadway.

Day 3-4: Washington, D.C. - Visit the National Mall, Smithsonian museums, and historic monuments.

Day 5-7: Philadelphia & Boston - See the Liberty Bell, Freedom Trail, and enjoy historic city centers.

10-Day Itinerary: Canada Rockies & Cities

Day 1-3: Vancouver - Explore Stanley Park, Granville Island, and Capilano Suspension Bridge.

Day 4-6: Banff & Jasper National Parks - Hike around Lake Louise, Icefields Parkway, and Athabasca Glacier.

Day 7-8: Calgary - Gateway to the Rockies, with cowboy culture and city vibes.

Day 9-10: Toronto & Niagara Falls - Finish with Canada’s largest city and the iconic waterfall.

2-Week Itinerary: Mexico Culture & Coast

Day 1-3: Mexico City - Explore Zócalo, Frida Kahlo Museum, and Teotihuacán pyramids.

Day 4-5: Oaxaca - Known for mezcal, colonial charm, and vibrant markets.

Day 6-8: Yucatán (Mérida & Chichen Itza) - Discover Mayan ruins and cenotes.

Day 9-14: Cancun & Riviera Maya - Relax on beaches, snorkel in Cozumel, and enjoy nightlife in Playa del Carmen.

3-Week Itinerary: North America Highlights Loop

Week 1: U.S. West Coast - Start in San Francisco, drive Highway 1, stop in Los Angeles, and end in Las Vegas with a Grand Canyon side trip.

Week 2: Canada - Vancouver, Banff, and Toronto, with a quick flight to Montreal for European flair.

Week 3: Mexico - Mexico City, Chichen Itza, and a few beach days in Tulum or Cancun before departure.

Pro Tips for Traveling North America

Plan Ahead: Popular attractions like national parks and Broadway shows book up early.

Budget Smart: The U.S. and Canada can be pricey. Save by traveling off-season, using passes (like America the Beautiful park pass), and booking accommodations early.

Stay Connected: Consider a SIM card or eSIM for smooth navigation and communication.

Respect Local Rules: Tipping is customary in the U.S. and Canada. In Mexico, brush up on basic Spanish phrases - it goes a long way.

Pace Yourself: Distances are huge - don’t try to do everything in one trip. Pick a focus and save the rest for next time.

With endless places to visit in North America, the continent is ideal for first-time explorers and repeat travelers alike. Use this guide to spark your planning, then customize your journey to fit your style.