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Why Visit Chicago?

Chicago offers a unique blend of:

1. Architectural brilliance (Frank Lloyd Wright, The Bean, Willis Tower)
2. Lakeside serenity (Lake Michigan’s scenic shoreline)
3. Cultural richness (world-class museums, theaters, and jazz clubs)

 

 Chicago Street Food You Can't Miss 

1. Deep-Dish Pizza (It’s practically a food group)

Where to try: Lou Malnati’s, Giordano’s, Pequod’s

Tip: Go for individual-sized portions unless you're sharing. One slice is a meal!

 

 2. Chicago-Style Hot Dog

A beef frank topped with yellow mustard, onions, relish, tomato slices, pickles, sport peppers, and celery salt—all in a poppy seed bun.

Rule: Never ask for ketchup.

Best spots: Portillo’s, The Wiener's Circle, Gene & Jude’s

 

 3. Italian Beef Sandwich

Thin slices of seasoned roast beef on a long Italian roll, often dipped in gravy and topped with giardiniera (spicy pickled veggies).

Must-try: Al’s Beef, Johnnie’s Beef, Mr. Beef on Orleans

 

4. Tamales (Chicago-style)

Steamed in corn husks and often sold from carts outside train stations.

Try: Tamale Guy (a local legend) or authentic taquerias in Pilsen 

 

5. Garrett Popcorn

The famous “Garrett Mix” (cheese + caramel) is a sweet-savory delight.

Grab a bag: While walking Michigan Avenue

 

 6. Food Trucks

Head to Daley Plaza, Streeterville, or check Chi Food Truck Fest in summer for rotating trucks featuring:

1. Korean BBQ
2. Gourmet grilled cheese
3. Lobster rolls
4. Vegan street food Top Places to Visit
5. Millennium Park & Cloud Gate (The Bean)

Navy Pier – for lake views, live music, and the Centennial Wheel
 

Art Institute of Chicago

Skydeck Chicago (Willis Tower) – for those daring to stand on glass

Magnificent Mile – shopping, food, and photo ops

Chicago Riverwalk – scenic strolls, kayaks, and waterfront bars 

If you’ve always dreamed of seeing Times Square light up, walking through Central Park, or snapping that iconic photo with the Statue of Liberty, now’s the perfect time to visit New York 

 

Getting Around

1. CTA ‘L’ trains and buses are reliable and affordable.
2. Get a Ventra Card for multi-day passes.
3. Walking is great in most neighborhoods.
4. Avoid driving in the Loop—parking is expensive and traffic is dense. 

 

Where to Stay

Budget: HI Chicago Hostel, Freehand Chicago

Mid-Range: Hotel Versey, The Godfrey Hotel

Luxury: The Peninsula, The Langham, Four Seasons 

Pro tip: Stay near The Loop, River North, or West Loop to be close to major attractions and the best eats. 

 

Best Time to Visit

Spring (April–June) and Fall (September–October) offer pleasant weather.

Summer festivals are a blast (Taste of Chicago, Lollapalooza), but hotel prices spike.

Winter: Cold, but magical—perfect if you love ice skating and holiday lights. 

 

Chicago Travel FAQs 

Q1. Is Chicago safe for tourists?

 Yes, especially in well-traveled areas like The Loop, River North, and Lincoln Park. Like any big city, stay alert, especially at night and on public transit. 

Q2. Is Chicago walkable?

 Very! Downtown and nearby neighborhoods are easily explored on foot, with plenty of restaurants and landmarks clustered close together. 

Q3. Do I need a car in Chicago? 

Not really. Public transport is solid, and Uber/Lyft are everywhere. Parking is pricey and limited downtown. 

Q4. What’s a must-have local food besides deep-dish pizza?

 Definitely the Chicago hot dog and Italian beef sandwich. Try both from local joints, not chains. 

Q5. Any free things to do in Chicago?

1.  Yes! Try: Lincoln Park Zoo (free entry!)
2. Millennium Park concerts
3. Chicago Cultural Center tours
4. Chicago Riverwalk stroll
5. Beach days at North Avenue or Oak Street Beach 

 

Conclusion:

Even summer evenings can be cool near the lake.Tipping is standard – 15–20% in restaurants.

Download apps like Yelp (food), Ventra (CTA info), and SpotHero (parking). Planning a Trip? Need a sample 3-day itinerary, help finding budget hotels, or booking food tours? Flighta can help plan it all, tailored to your dates and budget.