Book Flights to Chicago, Illinois
Chicago — the City of Big Shoulders, the Windy City, the Second City — is the American Midwest's great metropolis: birthplace of the skyscraper and electric blues, home of the Art Institute, Millennium Park's Cloud Gate, Lake Michigan's 26 public beaches, and one of the world's great restaurant scenes. Chicago has two major commercial airports — O'Hare (ORD) and Midway (MDW) — served by virtually every major US airline.
O'Hare is United's massive global hub (500+ daily flights); Midway is Southwest's Midwest stronghold. FareOptic compares all fares to both Chicago airports simultaneously for the best deal.
Cheap Flight Deals to Chicago
*All above fares are one way/round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions.
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Why Visit Chicago, Illinois?
From the Art Institute's Nighthawks and Cloud Gate's skyline reflections to deep dish pizza and Buddy Guy's blues club, Chicago rewards exploration across every dimension — architecture, food, music, beaches, and culture.
The Art Institute of Chicago
America's Most Visited Museum After the MetThe Art Institute of Chicago — on Michigan Avenue facing Grant Park — is one of the greatest art museums in the world: Georges Seurat's A Sunday on La Grande Jatte (1886), Grant Wood's American Gothic, Edward Hopper's Nighthawks, Picasso's The Old Guitarist, Monet's water lilies, and the world's greatest Impressionist and Post-Impressionist collection outside France.
Impressionist Gallery
The Art Institute's Impressionist and Post-Impressionist collection — 30+ galleries on the second floor — contains Seurat's La Grande Jatte (displayed in its own room), 35 Monets, Renoir's Two Sisters (On the Terrace), Toulouse-Lautrec, Cézanne, and Gauguin. Arrive when the museum opens (10:30am) to see La Grande Jatte before afternoon crowds
Millennium Park and Cloud Gate
Chicago's Most Iconic Public SpaceMillennium Park — 10 hectares in the heart of the Loop — contains Cloud Gate ('The Bean' — Anish Kapoor's mirror-polished sculpture reflecting the Chicago skyline), the Jay Pritzker Pavilion (Frank Gehry stainless steel bandshell hosting free summer concerts), Crown Fountain, and the BP Bridge. Cloud Gate is one of the most photographed public sculptures in the world.
Cloud Gate at Night
Cloud Gate after dark — when the Chicago skyline reflects in the polished ellipsoid from below — is arguably the most visually extraordinary public sculpture experience in the US. The walk-under space (the omphalos, or navel) where the sculpture's convex underside creates infinite mirror reflections is not to be missed
The Chicago Riverwalk and Architecture
America's Greatest Architectural CityChicago's architectural heritage — first skyscraper in the world (Home Insurance Building, 1885), Louis Sullivan's ornamental ironwork, Frank Lloyd Wright's Prairie Style origins, Mies van der Rohe's International Style, the Skidmore Owings & Merrill skyscraper tradition — makes it the greatest architecture city in North America. The Chicago Architecture Center on the Riverwalk offers excellent boat tours of the Chicago River canyon.
Architecture Boat Tour
The Chicago Architecture Center's 90-minute river boat tour (€50, book ahead) passes 50+ historically significant buildings with expert narration — the best single way to understand Chicago's architectural significance. The Chicago River canyon of glass towers is especially dramatic from the water. The Architecture Center itself has free exhibits on Chicago building history
Navy Pier and the Lakefront
Chicago's Spectacular Lake Michigan WaterfrontChicago's 29 km of Lake Michigan shoreline is one of the great urban waterfronts in the world: 26 public beaches (no admission), the 18 km Lakefront Trail (cycling and running), Navy Pier (Ferris wheel, IMAX, Chicago Children's Museum), Museum Campus (Field Museum, Shedd Aquarium, Adler Planetarium), and Lincoln Park (free zoo, 1,200 acres).
Lake Michigan Beaches
Chicago's public lakefront beaches — all free, all accessible by CTA — are one of the great urban free amenities in the US. Oak Street Beach (most fashionable, adjacent to the Magnificent Mile), North Avenue Beach (most lively), and Montrose Beach (kiteboarding, volleyball, least crowded) are the most popular. Lifeguards on duty June–Labor Day
Deep Dish Pizza, Hot Dogs, and Chicago Cuisine
The Greatest American Regional Food CultureChicago's food culture is among America's most distinctive regional cuisines: deep dish pizza (Giordano's, Lou Malnati's, Pizzeria Uno — the originator — and Chicago Pizza and Oven Grinder), Chicago-style hot dogs (Vienna Beef, never ketchup, mustard/relish/sport peppers/tomatoes/celery salt on a poppy seed bun), Italian beef sandwiches (Al's Beef), and a world-class fine dining scene.
The Chicago Hot Dog Rule
The Chicago hot dog has a strict canonical preparation that any Chicagoan will defend: Vienna Beef frank, steamed poppy seed bun, yellow mustard, neon-green relish, diced white onion, tomato slices, a dill pickle spear, sport peppers, and celery salt. Never ketchup. Rick Bayless (Mexican cuisine), Stephanie Izard, and Grant Achatz (Alinea — molecular gastronomy) represent Chicago's high-end scene
Chicago Blues, Jazz, and Live Music
Birthplace of Electric Blues and House MusicChicago is the birthplace of electric blues (Muddy Waters, Howlin' Wolf, Buddy Guy moved North during the Great Migration and plugged in) and Chicago House music (Frankie Knuckles at the Warehouse, 1977 — the original house club). Buddy Guy's Legends (blues club), the Chicago Jazz Festival (Grant Park, September), and the Chicago House music scene continue these traditions.
Buddy Guy's Legends
Buddy Guy's Legends on South Wabash is the essential Chicago blues club — a intimate 550-person venue where Buddy Guy himself performs annually in January. The club hosts nightly live blues from Tuesday through Sunday. The Rock and Roll Hall of Fame has inducted the Blues Legends that shaped Chicago's music: Muddy Waters, Howlin' Wolf, Little Walter, Sonny Boy Williamson
How to Find Cheap Flights to Chicago
Two Airports: ORD vs MDW — Know Which to Fly Into
O'Hare (ORD, 27 km northwest) is United's massive hub with the most flights and international connections. Midway (MDW, 15 km southwest) is Southwest's hub with lower fares on domestic routes. Both connect to downtown via CTA 'L' train: Blue Line from ORD (45 min, $5), Orange Line from MDW (30 min, $2.50). Choose based on fare and city location.
Book 3–8 Weeks Ahead for Best Chicago Fares
Chicago is one of America's most visited cities with fierce airline competition — fare windows are well-established. O'Hare flights are cheapest 3–6 weeks out on weekday departures (Tue/Wed/Thu). Midway/Southwest fares are lowest 2–4 weeks out on their flexible no-change-fee model. FareOptic tracks both airports simultaneously.
Avoid Chicago in January–February (Wind and Cold)
Chicago's infamous winters (average January high: -3°C, wind chill making it feel -20°C) make November–March the off-peak travel period with the lowest fares. If you visit in winter, pack for extreme cold. Spring (April–May) and fall (September–October) are ideal: 15–25°C. Summer (June–August) is lively but busy and priced accordingly.
Chicago Hosts Major Events — Book Far Ahead for These
Chicago Air and Water Show (August — free lakefront show, one of the largest in the US), Lollapalooza (Grant Park, late July), Chicago Jazz Festival (September), Chicago Marathon (October — book 6+ months ahead), and St. Patrick's Day (Green Chicago River — one of the most spectacular public events in the US).
Airlines Serving Chicago (ORD / MDW)
United Airlines
O'Hare (ORD) — United's Largest HubUnited Airlines operates its largest hub at Chicago O'Hare (ORD), with 500+ daily departures to 200+ destinations worldwide. O'Hare consistently ranks among the world's top 5 busiest airports. United's ORD hub serves all major US cities plus Europe, Asia, Latin America, and the Pacific — making it one of the most connected airports on earth.
Key Routes
Chicago ORD to all 50 US states; ORD to London LHR, Frankfurt FRA, Paris CDG, Tokyo NRT, Beijing PEK, Hong Kong HKG, Sydney SYD; ORD to Toronto, Mexico City; United's full worldwide network
American Airlines
O'Hare Hub + Midway ServiceAmerican Airlines maintains a major hub at O'Hare (ORD), its third-largest hub after DFW and CLT. American serves 150+ destinations from ORD including Transatlantic routes. American also served Chicago Midway (MDW) historically — check FareOptic for current AA Midway availability.
Key Routes
Chicago ORD to Dallas DFW, New York JFK/LGA, Miami MIA, Los Angeles LAX, London LHR, Madrid MAD, Dublin DUB, Tokyo NRT; American's full domestic and international network
Southwest Airlines
Midway (MDW) — Southwest's Key Midwest HubSouthwest Airlines dominates Chicago Midway Airport (MDW), operating Midway as one of its primary hubs. Southwest serves 60+ destinations nonstop from MDW with no change fees. Midway is 15 km southwest of the Loop — close to the South Side and a fast trip downtown via the Orange Line El.
Key Routes
Chicago MDW to Las Vegas LAS, Denver DEN, Orlando MCO, Baltimore BWI, Dallas DAL, Phoenix PHX, Nashville BNA, Atlanta ATL, Los Angeles LAX — Southwest's full point-to-point domestic network from Midway
Things to Do in Chicago, Illinois
Essential Info for Your Chicago Trip
State
Illinois (IL) — Cook County; 3rd largest US city by population
Currency
USD — US Dollar
Time Zone
CST (UTC-6) / CDT (UTC-5) in summer
Airport Codes
ORD — O'Hare Intl (27 km NW); MDW — Midway (15 km SW)
ORD to Downtown
CTA Blue Line: 45 min, $5. Uber: $35–55.
MDW to Downtown
CTA Orange Line: 30 min, $2.50. Uber: $20–35.
Public Transit
CTA 'L' trains and buses cover the city; Ventra card recommended
Emergency Number
911
Most Popular Airlines
Best Airlines for Domestic & International Routes
Frequently Asked Questions on Travel to Chicago
Everything you need to know about booking cheap flights to Chicago, Illinois
What airports serve Chicago, Illinois?
Chicago has two major airports: O'Hare International Airport (ORD, 27 km northwest of downtown) — United's largest hub and a top global connection airport — and Chicago Midway Airport (MDW, 15 km southwest) — Southwest Airlines' key Midwest hub. Both connect downtown by CTA L train: Blue Line from ORD, Orange Line from MDW.
Which Chicago airport should I fly into?
O'Hare (ORD) has more flights, more airlines, and all international routes. Midway (MDW) has cheaper Southwest fares on domestic routes and is closer to downtown. For flexibility and international connections, use ORD. For cheap nonstop domestics, compare MDW. FareOptic searches both airports simultaneously.
What is Chicago known for?
Chicago is known for its architecture (first skyscraper, Mies van der Rohe, Frank Lloyd Wright origins), deep dish pizza, electric blues and house music, Lake Michigan waterfront and beaches, the Art Institute (Nighthawks, La Grande Jatte), Cloud Gate in Millennium Park, the Chicago Bulls and Bears, and one of America's greatest restaurant scenes.
How do I get from O'Hare (ORD) to downtown Chicago?
CTA Blue Line 'L' train from O'Hare to downtown (Clark/Lake or Washington stations) takes 45 minutes and costs $5. Trains run 24/7. Uber/Lyft to downtown: $35–55 (25–45 min depending on traffic). Chicago is one of the best US cities for airport-to-downtown public transit.
How do I get from Midway (MDW) to downtown Chicago?
CTA Orange Line 'L' train from Midway to the Loop (Adams/Wabash) takes 30 minutes and costs $2.50. Trains run from 4am to 1am. Uber/Lyft to downtown: $20–35 (20–30 min). Midway is closer and cheaper to reach downtown than O'Hare by train.
What is the best time to visit Chicago?
June–August: summer festivals (Lollapalooza, Air & Water Show), beach season, 25–30°C. September–October: Chicago Jazz Festival, Chicago Marathon, fall foliage, 15–22°C — ideal weather. May: spring, comfortable, fewer crowds. March–April: cold and unpredictable. January–February: extreme cold, lowest fares.
What is the Chicago Architecture Boat Tour?
The Chicago Architecture Center (111 E. Wacker Drive, on the Riverwalk) offers 90-minute narrated river boat tours passing 50+ architecturally significant buildings along the Chicago River canyon. The tour (approximately $50, book ahead) is the best way to understand Chicago's position as the world's most important 20th-century architectural city.
Is Chicago safe for tourists?
Chicago's tourist areas — the Magnificent Mile, River North, Lincoln Park, Millennium Park, Wicker Park, the lakefront — are generally very safe for visitors. Like any large US city, some neighborhoods require awareness at night. Stick to well-traveled areas, take CTA L trains (safe), and check local travel advisories. The lakefront is populated and safe during daylight.
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