34 days in Chicago & Saint Louis Itinerary

34 days in Chicago & Saint Louis Itinerary

Created using Inspirock United States tour planner

Make it your trip
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Chicago
— 28 nights
Fly
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Saint Louis
— 3 nights
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Saint Louis
— 2 nights
Fly

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Chicago

— 28 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore the numerous day-trip ideas around Chicago: Swallow Cliff Stairs (in Palos Park), Oak Savannah Trail (in Griffith) and Willow Springs (Little Red Schoolhouse & Centennial Bike Trail). There's lots more to do: explore the world behind art at The Art Institute of Chicago, get a new perspective on nature at Field Museum, take in panoramic vistas at Skydeck Chicago - Willis Tower, and get curious at Museum of Science and Industry.

To find reviews, maps, other places to visit, and other tourist information, you can read our Chicago day trip site.

If you are flying in from Mongolia, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In September, plan for daily highs up to 30°C, and evening lows to 19°C. Finish your sightseeing early on the 13th (Sun) to allow enough time to fly to Saint Louis.

Things to do in Chicago

Parks · Outdoors · Museums · Trails

Side Trips

Saint Louis

— 3 nights

Gateway to the West

Test the local claim that Saint Louis is second only to Washington, D.C. in the number of free activities available by spending your holiday exploring the city's central neighborhoods, famous for their restored century-old red-brick buildings.
Start off your visit on the 14th (Mon): enjoy breathtaking views from The Gateway Arch, then stroll around Forest Park, and then pause for some serene contemplation at Cathedral Basilica of Saint Louis. Get ready for a full day of sightseeing on the 15th (Tue): examine the collection at Cardinals Hall of Fame and Museum, then take in nature's colorful creations at Missouri Botanical Garden, then savor the flavors at Food & Drink, and finally relax in the rural setting at Grant’s Farm.

For ratings, where to stay, more things to do, and tourist information, use the Saint Louis road trip planner.

You can fly from Chicago to Saint Louis in 3 hours. Alternatively, you can drive; or take a train. Traveling from Chicago in October, expect nights in Saint Louis to be about the same, around 11°C, while days are a bit warmer, around 26°C. On the 16th (Wed), wrap the sightseeing up by early afternoon so you can travel to Saint Louis.

Things to do in Saint Louis

Parks · Breweries & Distilleries · Tours · Museums

Saint Louis

— 2 nights

Gateway to the West

Start off your visit on the 16th (Wed): steep yourself in history at Old Courthouse and then test your team's savvy at popular escape rooms. Get ready for a full day of sightseeing on the next day: explore the world behind art at Saint Louis Art Museum, meet the residents at Saint Louis Zoo, and then appreciate the extensive heritage of St. Charles Historic District.

Discover how to plan a Saint Louis trip in just a few steps with Inspirock's itinerary builder.

Finish your sightseeing early on the 18th (Fri) to allow enough time to fly back home.

Things to do in Saint Louis

Museums · Childrens Museums · Zoos & Aquariums · Parks

Side Trip