Things to do in Chicago
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Chicago: 360 Observation Deck & 48-Hour Hop-on Hop-off BusYou get 48 hours of unlimited bus access across Chicago's main attractions, admission to the 360 CHICAGO Observation Deck on the 94th floor with panoramic views, audio commentary in multiple languages, four digital walking tours, and real-time bus tracking through the Big Bus app. The observation deck time is scheduled at booking; the bus runs anytime during 10am–4pm, so you control the pace.Is it for me?Best for first-time visitors and families who want to see Chicago's main landmarks without renting a car or planning transfers — the fixed observation deck time and flexible bus schedule mean you control both the structure and the pace.
Chicago: Cloud Gate, Architecture & Grant Park Full DayYou start at Cloud Gate in Millennium Park, then spend 100 minutes touring Chicago's major architecture by vehicle and foot—the Wrigley Building, Trump Tower, Board of Trade, and more. In the afternoon, choose between the Art Institute of Chicago or 360 Chicago observation deck, then visit Grant Park and Buckingham Fountain. A professional guide and driver are included; optional museum or observation deck admission costs extra. The full day requires moderate activity and comfortable shoes.Is it for me?Book this if you want Chicago's main landmarks and architecture in one structured day without arranging transport, tickets, or timing yourself—the fixed itinerary and included guide handle all three, leaving you to show up with comfortable shoes and water.
Chicago Brewery Tour: 5 Micro Breweries with Homemade GuacamoleA 90-minute brewery expedition through five handcrafted micro breweries in Chicago's Fulton Market and Brewery District, led by a guide in English or Spanish. You start with homemade guacamole and tortilla chips prepared by Chef Carla, plus three 5-ounce craft beer tastings included; then walk to four more breweries where you order additional beers and stay as long as you want. All locations are within walking distance.Is it for me?At 90 minutes for the guided portion, this tour leaves your afternoon open—you can do it early and still have time for lunch or other plans, or stay longer at any brewery after the group portion ends. The walk between breweries means you're exploring the neighborhood itself, not just tasting beer in one spot.
Midway to Downtown Chicago: Private Luxury SUV TransferYou get picked up at the Midway curbside by a uniformed, background-checked driver in a private luxury SUV that holds your whole group and luggage. The service includes the transfer, all taxes and fees, gratuity, and 60 minutes of wait time if your plans shift. Available 24/7, with the driver's location sent to your phone so you know exactly when to head outside.Is it for me?Book this if you're traveling with a group or luggage and want to avoid the taxi line, rideshare surge pricing, and shared shuttle schedules—a fixed-price driver waiting at curbside means you walk out and go, no negotiation at the curb.
Chicago Airport Transfer: Private Sedan & WiFiYou're met at arrivals by a driver holding your nameplate and given a sedan with WiFi and water for the ride into Chicago. All fees are locked in before you land, and you receive driver and vehicle details by email so you know exactly who to look for. The transfer covers up to 18 miles and includes specialized infant seats if you need them.Is it for me?Book this if you want to skip the airport taxi line and arrive at your Chicago destination knowing exactly who's picking you up and what it costs — the nameplate and the confirmation email are what make that possible.
Chicago Full-Day Walking Food Tour: Cloud Gate to deep dishYou walk 5 hours through downtown Chicago, stopping for deep-dish pizza, a Chicago hot dog, Italian beef, Garrett's popcorn, and the original Palmer House brownie, with a local guide pointing out Millennium Park, Cloud Gate, the Riverwalk, and the Chicago Theater along the way. The tour includes all tastings and ends with a voucher for a free 2-hour bike or kayak rental to use within three days—perfect for extending your time on the water or the lakefront path.Is it for me?Book this if you want to taste Chicago's most famous foods and see the main landmarks in one day without arranging separate restaurant reservations, museum tickets, or transport—the guide handles the route and the stories, and the free bike or kayak rental lets you explore the lakefront on your own time afterward.
Serial Killer & Chicago Landmarks Bus Tour: True Crime HistoryA 90-minute guided bus tour of Chicago that weaves together the city's true crime past and its most recognizable landmarks. The route passes Wrigley Field, the Mag Mile, and sites connected to serial killers John Wayne Gacy and Jeffrey Dahmer, with a live guide in English and a surprise giveaway for passengers. Children from age 13 are welcome.Is it for me?This tour works well for small groups or solo travelers interested in Chicago's true crime history and willing to spend 90 minutes on a bus; the fixed route and schedule mean the day is planned for you, and the guide handles the narrative so you can focus on the sites and the stories.
Field Museum Chicago: SUE T-Rex & Gin Tasting TicketYou walk through all the Field Museum's open exhibitions—SUE the T-Rex, the gems hall, ancient Egypt, the Americas, and Native Truths—then select three tastings from their gin, vodka, rye, or beer menu before you go. The ticket is adults 21 and up, includes all entry fees, and takes roughly three hours if you're moving at a normal pace.Is it for me?Pick this if you want to see the Field Museum's main attractions without planning separate visits, and you're 21 or older—the tasting is a bonus that makes the ticket feel less like a standard museum day and more like an actual outing.
Midway to Chicago Downtown: Luxury SUV Transfer & Meet InsideYou receive your driver's details by text as soon as you land, meet him at baggage claim with a nameplate, and ride in a private luxury SUV to your Chicago hotel. The fixed price includes luggage help, 60 minutes of wait time, and all taxes and fees — no negotiating fare or waiting for a shared shuttle. The exact drive time depends on traffic, but the service runs around the clock.Is it for me?Book this if you want to skip the taxi line and shared shuttle hassle after landing — the driver meets you inside the airport with your name on a sign, handles your bags, and takes you straight to your hotel on a fixed price with no surprises.
Chicago to O'Hare Airport: Luxury SUV Transfer & Meet-GreetA professional driver meets you at your hotel with a name sign, loads your luggage, and drives you to O'Hare in a disinfected luxury SUV. You get bottled water, hand sanitizer, and 15 minutes of free wait time if your departure is delayed. The fixed price means no surprises at the curb, and you arrive at the airport calm and on schedule.Is it for me?Book this if you're staying at a Chicago hotel and want a fixed-price, no-negotiation ride to O'Hare—the driver handles the door and the luggage, which is what turns a transfer into one less thing to manage before your flight.
Chicago O'Hare Airport Transfer: Luxury SUV with Hotel PickupYou're picked up from your Chicago hotel in a luxury SUV with a professional chauffeur who arrives early and knows the fastest route to O'Hare. The vehicle includes bottled water, phone chargers, and air conditioning; the driver handles your luggage and confirms your flight details so you can focus on getting to the gate. Pricing is fixed in advance, and you receive a receipt.Is it for me?Book this if you're traveling from a Chicago hotel to O'Hare and want to skip the parking garage, rental car, or ride-share guessing game—the fixed price and early arrival mean you're not managing logistics on travel day.
Chicago Flag Bus Tour: City landmarks and historyThe Journey of the Chicago Flag Bus Tour is a 90-minute guided bus tour through Chicago that traces the city's history from Fort Dearborn through the Great Chicago Fire to the World's Columbian Exposition, connecting each landmark to the symbols on the Chicago flag. The tour includes a live English-speaking guide, a skyline photo opportunity, and a surprise giveaway; children are welcome from age 13, and the pickup and drop-off point is near Millennium Park.Is it for me?The live English guide means you follow the stories as they unfold rather than through a recording, which works well if you're visiting Chicago for the first time and want the history woven together as a narrative instead of a checklist of sites.
360 Chicago: 94th Floor Views & Fast Pass EntryYou ride one of North America's fastest elevators to the 94th floor and spend time on an observation deck 1,000 feet above Chicago with 360-degree views of the skyline and Lake Michigan. Your fast pass skips the entry line, and you get access to CloudWalk's art installation, the interactive concourse exhibits, and CloudBar. Bring your phone for the Magnicity app, which identifies what you're seeing.Is it for me?Pick this if you want to see Chicago from above without spending time in an entry queue — the fast pass gets you straight to the elevator and the views, which is what makes a quick visit actually work.
Chicago Private Neighborhoods Tour: Gold Coast to ChinatownA private, four-hour tour of Chicago's most distinctive neighborhoods—Gold Coast Historic District, Lincoln Park, Hyde Park, University of Chicago, and Chinatown—with hotel pickup and an English-speaking local driver who shares stories and adjusts the route to your interests. Entrance tickets are not included unless specified, and your driver can suggest stops or wait while you explore on your own; the itinerary is fully flexible based on opening hours and what you want to see up close versus from the car.Is it for me?Four hours leaves room to move through all five neighborhoods without rushing, but not enough to linger inside museums or spend a full afternoon in any single area—ideal if you want a broad sense of Chicago's character and diversity in one outing, or if you're building this into a longer day with other plans.
Chicago: Christmas Eve Dinner Cruise Lake Michigan & DJYou board a dinner cruise on Lake Michigan, sit down to a chef-prepared three-course meal, and spend three hours watching the Chicago skyline from the water while a DJ plays and the bar stays open. The boat is wheelchair accessible, infant seats are available, and the fixed time means you know exactly when you'll be back on shore.Is it for me?Book this if you want to step out of the holiday rush for an evening and have someone else handle the meal, the timing, and the entertainment — the fixed three-hour window and included dinner mean you show up and the night unfolds without coordination.
Chicago Airport Transfer: Private Car & Curbside PickupYou book online, receive a confirmation with your driver's details, and get a text with their name and vehicle info when they're en route. Curbside pickup means no walking through a lot; your chauffeur loads your bags and drives you to your destination in a clean, air-conditioned car. A 15-minute grace period covers delays from baggage claim, and the full fare—including water and all taxes—is locked in before you arrive. Drop-off is handled smoothly, and you're done.Is it for me?Book this if you land with luggage and want to know the exact cost before you arrive—the fixed price and curbside pickup mean you skip the taxi line and the negotiation, which is what makes a tired arrival feel simple.
Chicago Field Museum: Skip-the-Line Ticket & Audio Tour AppYou get entry to the Field Museum plus a self-guided audio tour on your phone that covers the main highlights: Máximo the Titanosaur, Egyptian mummies, Lucy the ancient human fossil, SUE the T. rex, and the Nature Walk dioramas. Skip the line at Will Call, follow the app at your own pace, and avoid the confusion of figuring out what to see and why it matters.Is it for me?Best for anyone who wants to explore the Field Museum without waiting in line or following a group schedule — the app and ticket arrive together, so you move through the galleries at your own pace and hear the story behind what you're seeing.
Chicago to O'Hare Airport: Private TransferYou book a pickup time at your Chicago hotel, a driver arrives in an air-conditioned vehicle, and you're driven directly to O'Hare Airport (ORD) with fifteen minutes of free waiting time included. No surge pricing, no schedule to check, no negotiation — just a fixed price and a confirmed departure time.Is it for me?Book this if you want to remove the airport-morning scramble from your trip: no timing a train, no rideshare surge, no curb negotiation. The fixed price and confirmed pickup time mean you can focus on packing instead of logistics.
Chicago O'Hare & Midway: Wheelchair Accessible Airport TransferYou're met curbside at O'Hare or Midway by a licensed driver with a wheelchair-accessible Toyota Sienna WAV. The vehicle has secure restraints, bottled water is included, and the price covers gratuities — no surprises at drop-off. The service tracks your flight and reaches you by phone after landing so the driver's waiting when you clear arrivals.Is it for me?Book this if you're landing in Chicago and need a vehicle you can count on to be accessible and waiting — the private service and flight tracking mean you're not arranging transport after you land, which is what makes the whole arrival simpler.
Field Museum Chicago: SUE T. Rex & VR Experience TicketYou get entry to all general exhibitions—SUE the T. Rex, Ancient Egypt, the Gem Hall, China, and Native Truths—plus one VR experience of your choice when you arrive. No guide, no time limit within museum hours, no separate bookings for each section. Bring comfortable shoes and plan for at least three hours, though most people stay longer.Is it for me?Right for anyone spending a day in Chicago who wants to see the major natural history collections without planning multiple separate tickets or guided tours—the single admission covers everything, and the VR adds a different kind of seeing to the physical galleries.
