Planning a trip to Chicago? This ultimate Chicago Travel Guide will show you how to experience the best of the Windy City in just 2 days! Discover top Chicago tours and attractions, hidden gems, and a perfect 2 day itinerary for your Chicago weekend trip.
In this video, we’ll take you through a jam-packed 48 hours in Chicago, covering all the must-see Chicago attractions and sharing our best Chicago travel tips. This Chicago city guide has you covered. Get ready for an unforgettable Chicago vacation!
Some of the attractions are affordable even for a small budget. We take you with us and show you how and where you can best invest your dollars in CHICAGO.
In this video, we also mention a few things that you should know before you go.
And we explain why our Skydeck experience failed .
Tip: Pack layers, as the lakefront breeze can change the temperature rapidly .
See all POI mentioned in this video on Google Maps
https://www.google.com/maps/d/edit?mid=1mRo6K5-LVNyOd7aie3gLft-GvvC-bYM&usp=sharing
Here are the links to the operators and attractions mentioned in the video:
Navy Pier:
Walk the pier for views of the skyline, especially beautiful in the late afternoon. It’s FREE!
Visit Navy Pier in spring to enjoy SAKURA in Chicago. It’s also FREE !
Starbucks:
https://www.starbucksreserve.com/locations/chicago-roastery
360 Chicago:
https://360chicago.com/tickets
For the best photography, aim for the west-facing observation decks during the ‘Golden Hour’ to capture the sun setting over the urban grid.
Skydeck:
Chicago Water Taxi:
https://www.chicagowatertaxi.com
for 10$ you’re in!
Guided Boat Tours:
https://shorelinesightseeing.com
https://www.wendellaboats.com
Chicago Transit Authority:
https://www.transitchicago.com
*Tip: For this trip, prioritize the ‘Ventra’ transit pass for seamless L-train and bus access*
Chicago Chinatown:
Chicago Londonhouse:
https://londonhousechicago.com/rooftop/
00:00 – Welcome to Chicago: what’s in this video
00:26 – Day 1: Navy Pier
02:38 – Day 1: The Bean (Cloud Gate)
03:09 – Day 1: Magnificent Mile
03:38 – Day 1: 360 Chicago Observation Deck
10:31 – Day 2: Skydeck
14:05 – Day 2: Chicago Water Taxi
20:10 – Day 2: Chinatown
21:32 – Day 2: Londonhouse Rooftop Bar
Looking for a place to stay in Chicago? Watch this Hotel:
Disclaimer: We have not been commissioned or paid by anyone to create this video. The content corresponds to our personal opinion. We just enjoy this destination and would like to share it with you.
Subscribe to our channel to not miss more Chicago content coming soon!
https://www.youtube.com/@Destinations2see?sub_confirmation=1
#destinations2see #360chicago #chicagotravelguide #chicagotrip #chicagotravel #ChicagoWeekend
Music Credits:
Music from Uppbeat (free for Creators!):
https://share.uppbeat.io/2nke450lk6b5
https://uppbeat.io/t/locran/sapporo
License code: NLR462SHMY0GZ1KL





Wow, Chicago looks so beautiful! Definitely need to visit this amazing city, thank you for sharing this!!!
Great Chicago vibes!
Loved the mix of top spots and hidden gems , super easy 2‑day guide.
🤗🤗🤗🤗Beautiful video of places to go while visiting Chicago. Love the view of the city especially at night!
👍👍Thumbs up 71 and hope you have a wonderful Monday!
Beautiful city. Warm wishes from the team at Millionaire Paul's
Beautiful place, enjoyed the scenery and sightseeing. Wonderful tour. Have a great day. Greetings from Cebu Philippines
L65
Norie
Wonderful and amazing 🤩 city 🌆🌆
Fantastic and beautiful sharing ❤😊❤❤
terima kasih banyak sharingnya sahabatku
bagus, sangat menarik
semoga semakin sukses. L61
Beautiful city. Wonderful tour and place. Like # 59.
Looks so tasty food. Lovely flowers. Excellent video my Friend.
Great buildings. Thank you for sharing this beautiful video and presentation.
Amazing Chicago travel trip! Happy week my friend 👍🏻57
Such a relaxing staycation vibe in Chicago 🇺🇸✨ The mix of skyline views, Riverwalk strolls, cozy hotels, and evening lights creates the perfect 2-day escape—peaceful, stylish, and full of beautiful city energy!
Thank you for sharing the beautiful video in Chicago. The wonderful buildings and flowers are also pretty. Have a good time, my friend~ ❤
I love Chicago😍😍😍😍
Great tour around Chicago! We’ve been there a few times, there’s so much to see, and great shopping too! We enjoy the Art Museum!! 👌👍👍 Enjoyed the video, thanks!
Nice watching the beautiful video
Beautiful Work! 👍👀👍💯 I worked in and out of there for years with the railroad… you always do such a Wonderful job on your videos! 💯
So much great information in this video of what there is to see and do in Chicago. The views from the Observation Tower were pretty special, especially with the sunset in the distance, a perfect time of day to be up there. It looks like a fantastic city to spend a few days.
Great sharing. Love the colors you bring out.
Wonderful travel adventure, thanks for taking us along! Have a great week!
What a beautiful and awesome cityscape! Thank you for sharing this budget-friendly 2 days travel itinerary through Chicago, my dear friend! Your video makes me want to rush to Chicago! See you! Have a wonderful day! From 100tourkorea!
Like 45 👍
An amazing visit to Chicago. We enjoyed the sights and scenery. The Bean was very interesting. And the views from 360 Chicago were spectacular. Thanks for sharing the awesome views with us, have a wonderful week
Back in Chicago! That's great.
Wow, a resl nice presentation from your walk at this great place👍
Beautiful video guys! One of the places that is super high on our bucket list! Great tips and locations! and great to see the city from that water taxi, it always adds so much visiting cities from that viewpoint! Thanks for sharing guys ☺️🧡
Hello, friends! I hope you're doing well and that you continue to post such splendid videos here for us to enjoy and watch!!~
Beautiful Chicago landscape. There are many iconic statues and interesting spots here.
Thank you for the great Chicago sightseeing tips !
Chicago seems like such a vibrant city, we really loved this look at it!
great Destination
thank you for sharing
iconic❤❤
Very nice video! Chicago is such a great city with a lot to do. You did quite a lot. Thank you for sharing your visit!
The Bean looks very unique as a tourist attraction. Many thanks. 🙂
Hallo! Sehr hilfreicher Reiseführer für Chicago! Besonders der Tipp mit dem Wassertaxi als günstige Alternative ist klasse. Die Aufnahmen von der Londonhouse Rooftop Bar war toll. Frohe Ostern!🌷🐰
Looks like a fun couple of days in Chicago! The bean is a very iconic spot for the city, but yes it is busy. You had some excellent views of Chicago from the Chicago Observation Deck. I have been up there, but it was several years ago. Major bummer that is was so foggy when you went up onto the Skydeck. Yes the water off of the Great Lakes can change the weather quickly. The water taxi looks fun and great way to see the city. Enjoy your day! 😊👍
Hello. What a super helpful itinerary! 😍 It's great how you've managed to condense the highlights into just two days.🤩 Especially the tips for the architecture tour and the deep-dish pizza experience.🙂 Fantastic work! 😉Thank you so much. Best regards.🤗
Chicago looks absolutely fantastic. Definitely a place on my bucket list 🤠
What a gorgeous city! The cherry blossoms on Navy Pier are stunning! and the Sky deck looks like a ton of fun! Thanks for sharing Chicago with us!
Hello, dear friend.
Nice content.
I went to Chicago when I was a university student.
I'd like to go again with my daughter.
Thank you very much.
Have a great day! 👍27
woww this is so wonderful
We have been to Chicago several times over the years and always enjoy our visit. You covered a lot of ground and hit lots of the highlights in just two days. Thanks for sharing your travels with us!
Fantastic location and wonderful sights to see and things to do. Great tips as well. The views from the observation deck is amazing! Very much enjoyed watching. Best wishes, Matt & Bec 😊😊❤
Looks like a beautiful place to visit and nice balance between city and nature ❤ enjoyed exploring the city
Eine schöne Tour durch Chicago mit vielen Tipps! 🤩🤩Vielen Dank fürs Teilen und eine schöne Woche! 😊😊🐷