7 Chicago History Tours Worth Booking

1.Chicago in a Day: Food, History & Architecture Walking Tour

★★★★★★★★★★5.0 · 1,153 reviews · 4 hours 30 minutes (approx.) · from $100Our pick

Spend about 4.5 hours walking Chicago with a local guide such as Dave, Rich, Dash, or John. See the Chicago Theatre, Pedway, Riverwalk, Wrigley Building, Tribune Tower, Millennium Park, and The Bean while sampling deep-dish pizza, popcorn, a Chicago hot dog, Italian beef, and other local treats. The group is limited to 12 people.

“From beginning to end the tour was a fantastic way to see the city. Dave was an amazing tour guide who gave us the perfect balance of historical facts at each stop, time to wander, keep us moving to the next destination, and even was photographer to us for lots of landmarks! This was an awesome way to see Chicago and you could feel Dave’s love for the city ooze through every time he shared his knowledge at each stop. I would highly recommend!”

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2.Chicago: Field Museum of Natural History Ticket or VIP Tour

★★★★★★★★★★4.7 · 717 reviews · 1 day · from $29Best value

Choose a one-day Field Museum visit with general admission, a Discovery Pass, an All-Access Pass, or an Early Access VIP Tour. See Sue the T. rex, Maximo the Titanosaur, ancient artifacts, gems, Chinese jade, and the Lions of Tsavo. The VIP option includes a one-hour English tour for groups of up to 20 before opening.

“Love Fields, one of the best Natural history museum, if not the best, in the world!”

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3.Field Museum of Natural History Admission Tickets

★★★★★★★★★★4.5 · 489 reviews · 4 hours (approx.) · from $29

Spend about four hours exploring Chicago’s Field Museum, from 23 Egyptian mummies and Inca temples to SUE, the most complete T. rex ever found. Admission includes general and ticketed exhibits, plus free daily docent-led tours. Add a 3D movie for an extra charge, and arrive early if you want a preferred showing.

“Loved the live reptile exhibit and the underground exhibit. Visiting SUE is always a +. We visited mid week the last week of August so the museum was less crowded.”

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4.Chicago Walking Tour: Historic Treasures of Chicago

★★★★★★★★★★5.0 · 362 reviews · from $35

Walk from the Chicago Architecture Center through the Loop with a certified guide, stopping at the Wrigley Building, Palmer House, Carbide and Carbon Building, Reliance Building, and Chicago Cultural Center. Guides such as Bob, John, Jim, and Maureen have led memorable tours, with plenty of time for questions and architectural detail.

“What an amazing tour! Our guide Jim was so friendly and informative! We had already done other architecture tours so we were not too sure if this would be appealing to us but hands down it was awesome!! Definitely would recommend it aRead more”

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5.Chicago: Food, History and Architecture Tour

★★★★★★★★★★4.8 · 104 reviews · from $99

This 4.5-hour small-group walk pairs Chicago architecture and Prohibition stories with three local food samples. Guides such as Dave, Dash, and Rich lead you through the Pedway, Riverwalk, landmark buildings, and Millennium Park’s Bean. Expect 3 to 4 miles of walking, a full meal’s worth of tastings, and plenty of practical city tips.

“Great tour, highly recommended! Dave was a thoroughly engaging, and knowledgeable guide who clearly has a passion for history and architecture. My only recommendation is to include the food stops earlier in the tour since it's unlikely that guests have eaten lunch prior to a 1 PM food/architecture tour.”

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6.Chicago: Historic Gangsters & Twilight Tales Night Cruise

★★★★★★★★★★4.1 · 63 reviews · from $45

Cruise the Chicago River for 1.5 hours as an English-speaking guide connects glowing landmarks with stories of the Eastland disaster, the Chicago Fire, H. H. Holmes, mobsters, and reported hauntings. Meet at the First Lady box office near Michigan and Wacker. Drinks can be purchased onboard, but food is not included.

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7.Chicago: Historic Architecture Chicago River Small Boat Tour

★★★★★★★★★★4.6 · 26 reviews · 1h 30m · from $67

You’ll board a small historic yacht for a 90-minute cruise along the Chicago River, viewing more than 50 notable buildings while an English-speaking guide explains their design, builders, and place in Chicago’s story. Coffee, lemonade, sodas, and snacks are included. Arrive early for the best seat.

“We enjoyed the smaller feel of this tour vs others that have hundreds of people, but we had a hard time hearing the guide. We were at the front of the boat and between the people around us talking nonstop and the low volume of the speaker, we only heard about half of the tour. This wasn’t the guide’s fault, he was humorous and knowledgeable, but it did affect how much we learned while on the cruise. I also highly recommend arriving very early. Instructions said come 15 mins early and we got there 30 mins early to be safe, and almost every single seat was already taken. Overall, I…”

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