Chicago guides
Chicago rewards even a short stop with world-class architecture along the river, a free and open lakefront, serious museums and a food scene built on Italian beef, deep dish and neighborhood taquerias, all reachable by train from O'Hare and Midway.
Layover guides for Chicago
O'Hare International Airport (ORD) layovers
6 hoursHow to Spend a 6 Hour Layover in Chicago: O'Hare to the Bean and Tiffany Glass
A 6 hour layover in Chicago from O'Hare is enough for one compact loop: the Picasso, the Cultural Center's Tiffany dome and Millennium Park, all a short walk from the Blue Line.
8 hoursHow to Spend an 8 Hour Layover in Chicago: O'Hare to Art and Italian Beef
An 8 hour layover in Chicago from O'Hare is the right size for the Art Institute's greatest hits, a riverside stroll and a dripping Italian beef at Mr. Beef.
10 hoursHow to Spend a 10 Hour Layover in Chicago: O'Hare to Skydeck and the Rookery
A 10 hour layover in Chicago from O'Hare covers a Route 66 diner breakfast, the Skydeck glass Ledge, the Rookery's light court and the library's Winter Garden.
12 hoursHow to Spend a 12 Hour Layover in Chicago: O'Hare to Lincoln Park and Deep Dish
A 12 hour layover in Chicago from O'Hare stretches to Lincoln Park: a free zoo, the Nature Boardwalk, North Avenue Beach, the 360 Chicago deck and deep dish at Lou Malnati's.
Chicago Midway International Airport (MDW) layovers
6 hoursHow to Spend a 6 Hour Layover in Chicago: Midway to Chinatown Dumplings
A 6 hour layover in Chicago from Midway fits a quick Chinatown run: the riverfront pagoda at Ping Tom Memorial Park, soup dumplings at Hing Kee and egg tarts from Chiu Quon.
8 hoursHow to Spend an 8 Hour Layover in Chicago: Midway to Pilsen and Mexican Art
An 8 hour layover in Chicago from Midway pairs a quarry turned park in Bridgeport with Pilsen carnitas and the free National Museum of Mexican Art.
10 hoursHow to Spend a 10 Hour Layover in Chicago: Midway to the Field Museum
A 10 hour layover in Chicago from Midway reaches Museum Campus: SUE the T. rex at the Field Museum, Northerly Island, the Adler skyline view and a Jewish deli finale.
12 hoursHow to Spend a 12 Hour Layover in Chicago: Midway to Hull-House and Shedd
A 12 hour layover in Chicago from Midway connects Jane Addams' Hull-House, a Maxwell Street Polish at Jim's Original, the Shedd Aquarium and an evening in Chinatown.
Short trip guides for Chicago
Downtown Loop
3 hoursHow to Spend 3 Hours in Chicago: The Bean, Maggie Daley Park and a Rooftop
Three hours in Chicago is enough for the Bean, a stroll over the BP Bridge into Maggie Daley Park and a drink in the Chicago Athletic Association's Game Room or on Cindy's rooftop.
4 hoursHow to Spend 4 Hours in Chicago: Art Institute Icons and The Berghoff
Four hours in Chicago fits Crown Fountain, a focused tour of Art Institute masterpieces and schnitzel with house root beer at The Berghoff, a Loop original since 1898.
6 hoursHow to Spend 6 Hours in Chicago: Water Tower, Navy Pier and the River
Six hours in Chicago covers the Water Tower that survived the Great Fire, the skyline from Olive Park, Navy Pier, a Billy Goat cheezborger and the Riverwalk.
8 hoursHow to Spend 8 Hours in Chicago: Conservatory, Au Cheval and Skydeck
Eight hours in Chicago lets you ride the Green Line to Garfield Park Conservatory, eat an Au Cheval cheeseburger, stand on the Skydeck Ledge and stroll the Riverwalk.
Fitness guides for Chicago
FitnessChicago North Side Run to Montrose Harbor and an East Lakeview Day Pass
For a quieter Chicago run, start at FFC East Lakeview, head north through Lincoln Park, return along the shore past Montrose Harbor, and rinse off at the club.
FitnessChicago Lakefront Trail Run to Museum Campus and a Loop Day Pass
The best skyline run in Chicago is the Lakefront Trail from Ohio Street Beach south to Museum Campus and back through Grant Park, finished with a day pass and hot shower at Lakeshore Sport & Fitness Illinois Center.
About Chicago
Chicago is one of the easiest big American cities to see on a tight schedule, because both of its airports sit at the end of a rail line. The Blue Line runs from O'Hare into the Loop, and the Orange Line links Midway with the South Side and downtown. Between the river, the lakefront and Museum Campus, a few well-chosen stops show off world-class architecture, art and food without ever needing a car.