Start from the historic Michigan Avenue Bridge, take in the retro charm of the Tribune Tower and the elegant style of the Wrigley Building, and enjoy the scenery of the skyscrapers along both banks of the Chicago River. Visit the towering Trump Tower, experience the charm of "simplicity is the ultimate sophistication" at 330 North Wabash (formerly IBM Building/The Langham Chicago), and take photos with Marina City, known for its unique "corn cob" shape. Afterwards, you will arrive at the world of financial order — visit the Merchandise Mart, a global business center, and feel the perfect integration of culture and commerce at the entrance of the Chicago Opera House. Then explore the CME Group Building and witness its financial influence as the world's largest derivatives market. Next, tour the Willis Tower (formerly Sears Tower), once the tallest building in the world, visit the Chicago Board of Trade (CBOT), stop by the Federal Reserve Bank of Chicago, and appreciate Chicago's financial charm. Pass by the iconic Chicago Art Institute, a historic landmark founded in 1891, and admire its timeless architectural exterior. Finally, embark on your public space exploration journey: touch the mark of the starting point of Route 66, admire the exterior connotation of the top art museum, and interact with Cloud Gate in Millennium Park. Stop by the world-famous Buckingham Fountain, a grand illuminated fountain. Appreciate its magnificent architectural design and flowing waters, and experience the classic urban scenery and romantic vibe of Chicago while exploring the city’s iconic highlights. The tour concludes with a panoramic view of the city skyline, allowing you to savor Chicago's unique blend of architectural aesthetics, financial vitality, and cultural heritage.
Itinerary:
Tribune Tower + Wrigley Building + Michigan Avenue Bridge (20 mins) → Trump Tower + 330 North Wabash + Marina City (10 mins) → The Mart + Chicago Opera House + CME Group Building + Willis Tower (20 mins) → Chicago Board of Trade (CBOT) + Federal Reserve Bank of Chicago (10 mins) → The Art Institute of Chicago (Pass-by) → Historic Route 66 Begin Sign + Art Institute of Chicago + Millennium Park & Cloud Gate (30 mins) → Buckingham Fountain (10 mins) → Chicago City Skyline (10 mins)
Total Duration: 3 hours
1. Transportation (The type of vehicle used will base on the number of guests on the day).
2. English tour guide or driver-guide.
1. Food and beverage.
2. Attraction admission fee (Prices are subject to change without prior notice; Tickets should be purchased from the tour guide).
3. Service fee ( minimum US$15/person/day, Any child and Infant reserving a seat have to pay the service fees as well).
4. Any personal expenses are not listed in Fee Included.
“Ali Travel's service is excellent, and the advisors at every store are professional. We are two seniors and have travelled with them to Cuba, Yellowknife, the Dominican Republic, Cancún and China — every experience was fantastic.…”
“The whole trip went very smoothly. Canace was very professional — she managed the route and timing well and solved any issue promptly, which took a load off our minds. The pacing was just right: relaxed, not exhausting. A very go…”
“Ali Travel was great and professional, highly recommend! Their pricing was competitive and they had a lot of variety to choose from. I look forward to booking with them again for my next vacation!”
Verbatim excerpts from public Google reviews of Ali Travel’s five GTA stores — 4.4–4.7★ across 281 reviews as of August 2026. These are reviews of our service, not of this specific departure. Read all reviews on Google →
Reserve online and pay in full right away — this tour is priced below our standard CAD $300 per-person deposit, so one payment secures your booking. We then confirm availability, usually within 24 hours, and update your booking status.
Card details are entered directly into Moneris, Canada’s largest payment processor — your card number never reaches our servers.
Cancellation charges, from the date we receive written notice:
Once airline tickets have been issued, the air portion is non-refundable regardless of the schedule above.
Ali Travel Inc. is registered with the Travel Industry Council of Ontario as a travel retailer (#50025124) and wholesaler (#50026847) — both checkable on TICO’s public register. Ontario’s Travel Industry Compensation Fund may reimburse you if we, or an end supplier such as an airline, become insolvent and the travel is not provided.
The Fund has a per-person limit, exclusions and a claim deadline — TICO’s page sets out what it covers.
One named consultant stays with your booking from confirmation to your return — the same person for documents, seat and room requests, changes, and anything that comes up while you are away. Call (416) 560-5888 or visit any of our five stores across the Greater Toronto Area.
Passport names and dates of birth are needed because flights are ticketed in your legal name; we never sell your personal information, and it is shared only with the suppliers delivering this trip. Privacy Policy →
Per person · departures 15 Oct 2026–6 Oct 2027
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