Advertisement
Chicago Tours
Private Half-Day Tour of Chicago

Private Half-Day Tour of Chicago

By Tripshepherd Chicago Tours
What is Travelers’ Choice?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travelers and are ranked within the top 10% of properties on Tripadvisor.

Ages 0-120
Duration: 4h
Start time: Check availability
Mobile ticket
Live guide: English
More


  • VIP Private small group tour
  • VIP Transportation for your exclusive enjoyment
  • Luxury Mercedes Metris 7-passenger van
  • Private Tour Guide for exclusive fully narrated tour
  • Complimentary downtown hotel private pick up and drop off
  • All Attraction admissions, taxes and fees included
  • Skydeck Chicago - Observatory and The Ledge
  • Chicago Bean (Cloud Gate)
  • Architectural Sightseeing Cruise
  • Chicago Adler view point
  • Chicago Buckingham Fountain
  • Entry/Admission - Skydeck Chicago - Willis Tower
  • Entry/Admission - Adler Planetarium
What's not included
  • Gratuities (optional)


Start:Multiple pickup locations offered.
  • 238 E Monroe St, Chicago, IL 60601, USA
    If you are driving into Downtown Chicago and require parking, we recommend parking in the Millennium Park Garage located, 5 S Columbus Dr, Chicago, IL 60601, United States. It is an underground parking garage where you can park for the duration of your tour.
Pickup details
  • We offer complimentary hotel pick up and drop off in Downtown Chicago
Hotel pickup offered
During checkout you will be able to select from the list of included hotels.
    End:This activity ends back at the meeting point.

      • Wheelchair accessible
      • Stroller accessible
      • Service animals allowed
      • Near public transportation
      If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 87115P32

      • Confirmation will be received at time of booking
      • Most travelers can participate
      • This is a private tour/activity. Only your group will participate

      • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

      If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 87115P32

      Currently unavailable
      This product is unavailable to book via Tripadvisor.
      Explore other options
      Itinerary
      • 1
      • 2
      • 3
      • 4
      • 5
      About the operator
      Don’t take it from us – here’s what people have to say about this operator:
      • Tripshepherd Chicago Tours
        45
        Chicago, Illinois
        Joined in April 2017
      • sstanding
        0 contributions
        5.0 of 5 bubbles
        Best tour ever!
        Robert was the hands down the best tour guide we have ever had. He was professional, pleasant, and knowledgeable about the city. Everything was lined up for us, including tickets to the observation deck of the Willis (Sears) Tower, and the architectural boat tour. He accompanied us right through the check-in process. I would take this tour again in a heartbeat.
        Written September 26, 2024
      • sofiamW2277AX
        0 contributions
        5.0 of 5 bubbles
        Informative history of Chicago industry
        My daughter and I had a wonderful time. Andrew was very knowledgeable and had a deep understanding of the economy and industry history of Chicago. We were hungry and he adjusted his tour so that we could eat at a local place. He also gave good advice about getting around town. Highly recommended!
        Written August 24, 2024
      • 456edwigec
        0 contributions
        1.0 of 5 bubbles
        Unreliable company
        Very disappointed not to have been transferred to another company which could have offered a similar service (In this field they all know each other and this should have been handled differently and certainly more professionally, this isn’t a cheap tour). This was the only day I had in Chicago and treated myself with this tour. I am still waiting to hear back from my email as to get a refund. Here is the message I received 3 1/2 hr before the excursion was due: This message is regarding your Scenic Chicago Night Tour booked for tonight, Sat, Jul 20, 2024. Unfortunately, we are not able to provide the tour tonight due to our tour guide not being available. I have copied the two options we have for moving forward below: 1. We are able to reschedule your tour to tomorrow night at the same time, July 21 at 6:00 PM. 2. We are able to cancel your booking and provide a full refund. Please let me know which option works best for you, my apologies for the inconvenience and late notice. If you have any questions or concerns, please let us know. Sincerely, Liam
        Written July 21, 2024
      • 375lillyg
        0 contributions
        5.0 of 5 bubbles
        Chicago Downtown Tour
        This trip was amazing. We did not feel rushed and our guide was super amazing. The fact that we did not have to drive or park in the various places we visited was wonderful. At the end of the trip our guide was nice enough to drop us off where we had left our car and it was seamless. Constantly communicating we felt very well taken care of. We would do this again
        Written June 5, 2024
      • Z5385PUjoem
        0 contributions
        2.0 of 5 bubbles
        An Uber driver that includes pre-purchased tickets
        Sears tower is fun and so is the boat ride. However these can be easily purchased for about $70. The rest you're just paying an Uber to pick you up and drop you off. Not worth the cost. Guide was polite and friendly but not exceptionally insightful on the city. Fell below expectations.
        Written February 5, 2024
      • casey2220
        0 contributions
        5.0 of 5 bubbles
        Worth the expenditure
        Our tour went off without a hitch.Jake picked us up on time and was an excellent and informative guide.The architectural boat tour is a must and a sampling of the other parks and sites was well planned.
        Written November 6, 2023
      • janisb743
        0 contributions
        5.0 of 5 bubbles
        A very enjoyable tour
        Very enjoyable tour. Our guide was friendly, and knowledgeable. It was great to have him drop us off to view and then be there when we were ready to move on. We saw all the highlights of the city. Because it was a Saturday the skydeck was very crowded and we decided not to wait 20 minutes to try the edge. All in all I would be happy to do this tour again, just not on such a busy day.
        Written October 26, 2023
      • Spellingchamp76
        0 contributions
        5.0 of 5 bubbles
        Lots to see. Lots to do. No surprises. Yay!
        First time in Chicago. Everything was as promised. I really felt like I got to do a lot in a relatively short amount of time. Oh the pictures you'll get on the cruise down the Chicago river. Wow!! Tour guide was friendly and was detailed in where to find him after each leg of the excursion. I recommend to all. Kinda' lovin' Chicago!!!
        Written October 25, 2023
      • bethjJ4572WQ
        0 contributions
        5.0 of 5 bubbles
        Do this one!
        Great tour! The driver/guide was very informative, and made great use of our time. I grew up in the burbs, and my kid had never been to Chicago. We both learned alot, got great photos, and had a memorable time I have a service dog, and there were no hang ups or issues from him coming along
        Written October 17, 2023
      • Seth W
        0 contributions
        5.0 of 5 bubbles
        Great Experience
        Great experience with Joe & Matt. They had countless facts & history to share about Chicago, and it was a lot of fun to learn about the city. We saw a bunch of iconic sights on the city, and had a blast.
        Written October 15, 2023
      • lauracD65IG
        0 contributions
        5.0 of 5 bubbles
        well worth the money
        Danny was very knowledgeble on the highlights of the city. He made sure we got to each place and had the right amount of time, before moving on to the next spot. We got to see the Buckingham fountain all lit up, we saw the Bean at night, and got to see the The Ledge at the top of the Willis Building. He pointed out all the interesting spots, taught us about the history of the city, and made a few quick spots for us to take pictures. Overall, this tour beat my expectations
        Written September 30, 2023
      • BoardingPass311211
        0 contributions
        5.0 of 5 bubbles
        Chicago History
        Danny was amazing with the information he shared about Chicago and I loved how there were only 3 of us on the tour. That made it more personable.
        Written August 8, 2023
      • 118liliag
        0 contributions
        5.0 of 5 bubbles
        Best of Chicago Small Group Tour - See Sight Tours
        Great and Amazing tour of the most iconic spots in the city of Chicago. I highly recommend this tour and See Sight Tours. Jake was incredible and very knowledgeable.
        Written July 23, 2023
      • 34cassiee
        0 contributions
        5.0 of 5 bubbles
        All the things
        This tour was amazing!! Joe was great!! Very knowledgeable and had a ton of awesome recommendations of places to see and visit in Chicago. I feel like we hit most of the must see tourist spots in the city. Skydeck was my favorite! I love it and look forward to my next visit to see even more!!
        Written May 22, 2023
      • milianst
        0 contributions
        5.0 of 5 bubbles
        Great intro to Chicago
        Danny was great! Communication was thorough and gave us good recommendations. We got to see the highlights of Chicago including the River Architecture tour, the bean, the Sears (Willis) tour and Chicago theater.
        Written April 8, 2023
      See all 45 reviews
      These reviews are the subjective opinions of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
      No reviews yet. Be the first to share your thoughts!
      *Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.

      Private Half-Day Tour of Chicago provided by Tripshepherd Chicago Tours

      All Chicago HotelsChicago Hotel DealsLast Minute Hotels in Chicago
      All things to do in Chicago
      RestaurantsFlightsVacation RentalsTravel StoriesCruisesRental Cars