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Steal My 48-Hour Chicago Itinerary ✈️
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items Planning a quick trip to Chicago? Here's my exact 48-hour itinerary, including where to stay, what to do, where to eat, and the travel essentials that made my trip easier.
Map
Sections
7
Where to Stay
Travel Tools I Used
How I Got Around Chicago
Day 1: Downtown Chicago
Day 2: Museums & Shopping
Where I Ate
Where to Stay
Where I stayed during my 48-hour trip to Chicago and why I'd recommend it to other travelers.
I stayed here during my Chicago trip and loved having easy access to the airport and public transportation. A great option for travelers looking for convenience and value while exploring the city.
Holiday Inn Chicago O'Hare Area by IHG
Travel Tools I Used
The apps and tools that helped me stay connected, navigate the city, and access my itinerary throughout the trip.
One of the best travel upgrades for my Chicago trip. I had mobile data as soon as I landed, making it easy to navigate the city, use the Ventra app, access my itinerary, and stay connected throughout my trip without worrying about finding Wi-Fi.
Holafly
My secret weapon for planning Chicago! I used Wanderlog to organize my itinerary by neighborhood, map out restaurants and attractions, and keep everything in one place. Perfect for maximizing every hour of your trip.
Wanderlog app
How I Got Around Chicago
How I explored Chicago using public transportation and saved money on transportation costs.
Instead of relying on rideshares, I used Chicago's public transportation system throughout my trip. Adding my Ventra Card to Apple Wallet made every ride seamless, and reloading it was incredibly easy. I highly recommend it if you want to save money ...
Ventra Card
Day 1: Downtown Chicago
A day exploring some of Chicago's most iconic landmarks, skyline views, and waterfront attractions.
If you're visiting Chicago for the first time, Millennium Park should be at the top of your list. It's home to some of the city's most recognizable landmarks and offers amazing photo opportunities right in the heart of downtown
Millennium Park
A must-see attraction and one of the best photo spots in the city.
Cloud Gate
I loved walking along the Chicago Riverwalk and taking in the incredible architecture. It's a great place to slow down, enjoy the views, and see why Chicago is famous for its skyline.
Chicago Riverwalk
I spent some time exploring Navy Pier and loved the mix of lake views, city views, and lively atmosphere. It's a great spot to walk around, grab a bite to eat, and experience a different side of Chicago.
Navy Pier
One of my favorite stops in downtown Chicago. The historic architecture and famous marquee make it a perfect photo spot and a classic Chicago experience.
The Chicago Theatre
If you're looking for one of the best skyline views in Chicago, LH Rooftop is worth adding to your itinerary. The views of the river, historic buildings, and surrounding skyscrapers are absolutely stunning, especially around sunset.
LH Rooftop
Day 2: Museums & Shopping
A mix of culture, science, and some budget-friendly shopping before heading home.
One of the largest science museums in the world and a must-visit for aviation, technology, and innovation enthusiasts. I especially enjoyed exploring the transportation and aviation exhibits, which made this one of the most interesting stops of my tr...
Griffin Museum of Science and Industry
One of my favorite stops for finding great deals on clothing, accessories, and travel essentials. A great option if you're looking to shop without breaking the budget.
Burlington
Perfect for affordable fashion, basics, and accessories. I found a variety of trendy pieces at very reasonable prices and loved browsing through the multiple departments.
Primark
Another great spot for bargain shopping. I enjoyed looking for discounted brand-name clothing, beauty products, and travel essentials at affordable prices.
Ross Dress for Less
Where I Ate
The food and coffee spots that made my Chicago trip even better.
A must-try for anyone visiting Chicago. I stopped here to try the city's famous deep-dish pizza, and it definitely lived up to the hype. Perfect for experiencing one of Chicago's most iconic foods.
Giordano's
More than just a coffee shop, this multi-level Starbucks Reserve is an experience on its own. I loved exploring the different floors, trying specialty drinks, and taking in the beautiful design of the space.
Starbucks Reserve Roastery
A Chicago staple worth trying. I recommend it for the famous Garrett Mix, a delicious combination of caramel and cheese popcorn that makes for the perfect snack or souvenir from the city.
Garrett Popcorn
The best place to try a classic Chicago-style hot dog. I recommend it because it's a Chicago institution, serving this iconic local favorite with all the traditional toppings and a fun, casual atmosphere.
Portillo's & Barnelli's Chicago
Favorite Chicago Experiences
The experiences that made my Chicago trip unforgettable and that I'd gladly do again on my next visit.
One of the best budget-friendly experiences in Chicago. I got amazing views of the city's architecture and skyline from the river at a fraction of the cost of a traditional architecture cruise.
Chicago Water Taxi
Looking for skyline views without paying for Skydeck or other observation decks? LH Rooftop offers incredible views of downtown Chicago and the Chicago River, and visiting the rooftop is completely free. I loved visiting around sunset. It was one of ...
LH Rooftop