Chicago is America's great underrated city. The birthplace of the skyscraper still has the best architecture in the country, from Frank Lloyd Wright to Mies van der Rohe to Jeanne Gang. Add in world-class museums, a food scene that goes far beyond deep dish, and lakefront beaches in the middle of a metropolis. Chicago offers excellent value for a major city. Hotels are cheaper than the coasts, food is generous and affordable, and the public transit actually works. Flight deals to O'Hare are frequent. This is a city that deserves more visitors.
Best Time to Fly to Chicago
Peak Season
June through August brings festivals, beach weather, and the most tourists. Lollapalooza weekend in early August is especially crowded.
Off Season (Best Deals)
January through March is brutally cold but significantly cheaper. November has holiday markets without December crowds.
Summer (June to August) is warm at 70-85°F and perfect for the lakefront. Fall (September to October) is pleasant at 50-65°F. Winter (November to March) is harsh at 20-35°F with wind chill. Spring (April to May) is variable at 45-65°F.
💡Book 6-8 weeks ahead for summer festivals. Winter deals appear frequently with short notice.
Cheapest Months to Fly to Chicago
Cheapest Months
January, February, March
Most Expensive
June, July, August
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Must-Try Foods in Chicago
Deep Dish Pizza
Chicago's famous thick-crust pizza is more casserole than slice. Lou Malnati's and Giordano's are classics. Pequod's caramelized crust wins local votes. Order ahead; these take 45 minutes to bake.
$15-25
Chicago-Style Hot Dog
The Vienna beef dog is loaded with mustard, onions, relish, tomato, pickle, sport peppers, and celery salt on a poppy seed bun. Never ketchup. Portillo's is the institution. Available everywhere for a few bucks.
$4-7
Italian Beef
Thinly sliced seasoned beef on Italian bread, dipped in jus with giardiniera peppers. Order it wet (dipped) and hot (spicy peppers). Al's Beef is classic. The messier the better.
$10-15
Top Attractions in Chicago
Art Institute of Chicago
One of the world's great art museums houses Seurat's Sunday Afternoon, American Gothic, and an incredible Impressionist collection. The Modern Wing is stunning. Allow at least half a day. Thursday evenings are free for Illinois residents.
Architecture River Cruise
The Chicago Architecture Center's boat tour is the best way to understand the city's building heritage. Ninety minutes on the river with expert docents explaining the skyline. Book the first morning tour for fewer crowds.
Millennium Park & The Bean
Cloud Gate (the Bean) reflects the skyline in its mirrored surface. Surrounding Millennium Park has free concerts at Pritzker Pavilion, the Crown Fountain, and great people-watching. All free, all essential.
Daily Costs in Chicago
Chicago offers good value for a major city. Hotels are cheaper than New York or San Francisco. Food is generous and fairly priced. The L train keeps transport costs low.
Accommodation (per night, pick one)
Budget
$80-130
Mid-Range
$150-250
Airbnb
$100-180
Food (per day)
Street Meal
$8-15
Restaurant
$20-40
Coffee
$4-6
Transport
Local Transport
$2.50/ride
Comfortable Daily Budget
(excluding flights)
$100-160
Getting Around Chicago
From the Airport
The Blue Line runs from O'Hare to downtown in 45 minutes for $5. From Midway: Orange Line takes 30 minutes. Rideshares cost $35-50 from either airport.
Getting Around
The L train (elevated/subway) connects most tourist areas efficiently. Buses fill the gaps. Downtown is very walkable. Rideshares work well. Taxis are easy to flag downtown.
Tips
- •Buy a Ventra card for unlimited transit rides. $20 for a 3-day pass.
- •Walk the Riverwalk and Magnificent Mile. Downtown is very pedestrian-friendly.
Where to Stay in Chicago
The Loop / Magnificent Mile
Downtown Chicago has the architecture, museums, and lakefront. Millennium Park and the Art Institute anchor the area. Easy transit access everywhere. Start here for the classic Chicago experience.
Wicker Park / Bucktown
The hipster heart of Chicago has craft cocktail bars, live music venues, and late-night restaurants. More local than River North with better prices. Dive bars and upscale spots coexist.
Pilsen / Hyde Park
Pilsen has vibrant Mexican culture, street murals, and the National Museum of Mexican Art. Hyde Park has the University of Chicago, Frank Lloyd Wright's Robie House, and Obama's neighborhood.
Smart Travel Tips for Chicago
FAQs About Flights to Chicago
Chicago is moderate for a major city. Hotels and food are cheaper than coastal cities. Budget $100-140 per day for comfortable travel. The L train keeps transport costs low.
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