Chicago is a food and entertainment Goliath, taking on metropolitan giants like New York and Los Angeles. Home of Wrigley Field, Soldier Field, the Loop and the Magnificent Mile, chances are, you'll never see it all. But you can pick and choose the memory-makers you and your wallet will enjoy most.
Flights To Chicago
We searched for Wednesday round-trip flights about 6 weeks in advance. On arrival, Chicago's aboveground L Train runs from O'Hare International and throughout the city as an affordable in-town transportation option. If you're planning on flying, check out our guide to finding cheap airline tickets.
Flying from New York's LaGuardia, $81 on Spirit Airlines took us into Chicago's O'Hare International and back on 2-hour evening flights. Unfortunately, using downtown Chicago's Midway International ramped cost to $244 on Delta. However, from Philadelphia, United Airlines morning flights using Midway were $71.
Out of curiosity, we checked Amtrak and found a round-trip seat from Indianapolis with a dining car, carry-on baggage and free Wi-Fi for just $1! It was the last available seat on "851 Hoosier State" at 6 a.m. mid March, so don't expect free rides all the time. Still, that should give you an idea of the kind of rail deals you can snatch if you keep your eyes open.
From Atlanta, a $71 United fare would take you to O'Hare, but Midway cost $124 on morning Delta flights. Further south, flying from Fort Lauderdale-Hollywood International, Spirit had late-evening flights for $127 into O'Hare; flying early morning from Miami International into Midway was $187 on Delta.
Moving west, we checked out Dallas-Fort Worth, finding 2½-hour United midday flights for $71 into O'Hare; the best we could do on Southwest entailed evening flights using Dallas' Love Field and Chicago's Midway, totaling $120.
From Los Angeles' LAX, we found United flights. One originated in Ontario, California, with 1 stop in San Francisco, making airtime nearly 7 hours for $171; pay $190, and United used Santa Ana's John Wayne Airport and O'Hare, offering 4-hour-or-so trips for $190 total. Moving up to Portland, we found nonstop 4-hour evening flights using O'Hare on Spirit for $104; using Midway more than doubled that.
Hotels In Chicago
What can you get for your money in Chicago? Count beds and check Wi-Fi fees! Along the Magnificent Mile, Hyatt was $227 a night, $1,589 for a week, while nearby Courtyard by Marriott was $222 a night, or $1550 a week. Amenities like free Wi-Fi were similar, but you got 2 queen beds at the Hyatt versus 1 queen or a king and sofa bed at Courtyard.
Fairfield Inn was $213 a night and included a hot breakfast buffet, Wi-Fi and all amenities. With a "good" rating, Inn of Chicago had 1 queen bed for $146 a night, with neither Wi-Fi nor breakfast included. The Omni had a 2-queen-bed suite for $199, but Wi-Fi, breakfast and parking were extra. Unless you need Wi-Fi in your hotel room, you shouldn't have much trouble finding free Wi-Fi in chicago. Our guide to finding free Wi-Fi should give you an idea of places to look.
Stay outside the Magnificent Mile, and Homewood Suites in the northern suburbs at Lincolnshire was $113 a night for 1 king or 2 double beds, complete with full amenities, fitness center, pool, free Wi-Fi and free breakfast, too. Even on the Magnificent Mile, Homewood was $174 a night for a king suite and identical perks.
Airbnb easily yielded a comfy hardwood-floored 2-bedroom, 2-bath loft with queen beds on the South Loop for $130 a night ($1,153 for the week including fees) with a full kitchen and Wi-Fi. If you're an American Express rewards card member, you can redeem your Membership Rewards towards an Airbnb stay.
For wow factor, a River North luxury 1-bedroom with plate-glass views and slick modern furnishings was $139 a night, $1,260 for the week with fees. In a trendy neighborhood, with a fitness center, pool, rooftop patio and Wi-Fi, the apartment offered bird's-eye views of Chicago's good life beyond.
Eating Out In Chicago
"Deep-Dish City" regularly earns top honors as Best Food City. In past years, national People's Choice Food Awards have chosen Bar Toma for best pizza, Butcher and the Burger for best burger, and Hoosier Mama Pie Co. for baked goods. Gibson's took 2015's best steak. Try them, or check out some more affordable options.
For breakfast, Lou Mitchell's Restaurant and Bakery "preaches old-time restaurant religion," from coffee to malted pecan and bacon waffles. Pannenkoeken Café on Lincoln Square specializes in the "authentic Dutch Pannenkoek" as well as French toast and custom-built omelets, and both keep it around or under $10.
For best deep-dish pizza, try Giordano's, Gino's East, Lou Malnati's Pizzeria or Pequod's Pizza. For "cracker-thin-crust," channel Guy Fieri at Vito & Nick's Pizzeria on South Pulaski Road, or visit Coalfire, Piece Brewery and Pizzeria, Pizzeria Da Nella or Spacca Napoli Pizzeria.
Al's #1 Italian Beef delivers what it promises regular, wet, dipped or dry. Superdawg Drive-In offers a 100-percent beef hot dog experience plus everything else, including fountain creations.
The Billy Goat Tavern on Michigan Avenue will feed you "cheeseborgers," breakfast and more for about $5 from 7 a.m. until 10 p.m. Portillo's is a "Chicagoland tradition," with award-winning ribs, beef, hot dogs, salads, pasta, chocolate cake and shakes.
Package Deals On Attractions
Before you invest in packages, check your must-see attractions' websites and prices. Some, like the Art Institute of Chicago, are already free for kids under 14 or offer discounts to Chicago residents.
Others, like the Museum of Science and Industry, charge a la carte. Even among packages, some offer greater flexibility than others:
- The Chicago Choose 4 Explorer Pass includes 4 top attractions from a list of 20 or so. An adult pass costs $70; children are $46 each. Passes are good for 30 days after activation, and you receive a mobile-friendly or printable e-pass and guidebook with entertainment coupons.
- The Go Chicago Card offers 1-, 2-, 3- and 5-day all-you-can-do passes for $85, $120, $149 and $175 for adults and $60, $84, $99 and $119 for children, sometimes halving typical costs. You can also build a custom pass, but discounts are only 20 percent, and our 4 choices ran $88 per adult.
- CityPASS Chicago includes 5 select attractions for $98 per adult and $82 per child, a 53-percent savings. The 9-day pass provides entry to Shedd Aquarium, Skydeck Chicago and the Field Museum. You must choose between the Museum of Science and Industry and 360° CHICAGO; you must also choose between the Adler Planetarium and Art Institute of Chicago.
Chicago Attractions - Getting In Free
For Illinois residents, the Adler Planetarium, Shedd Aquarium, Field Museum, Museum of Science and Industry, and Art Institute of Chicago all offer free entrance on certain days. Make sure to check websites for dates.
Many attractions offer free admission to educators and active-duty personnel, as long as you register online.
Shedd Aquarium's website states that even "a valid Bank of America/Merrill Lynch ATM, credit, or debit card, along with photo identification," provides "1 free general admission on the first full weekend of every month."
Other attractions that offer free entrance to Bank of America credit card holders on the first full weekend of each month include: Art Institute of Chicago, Museum of Contemporary Art, Adler Planetarium (hours may vary), Chicago History Museum, National Veterans Art Museum (Saturdays only), The DuSable Museum of African American History, The National Hellenic Museum, National Museum of Mexican Art.
Always free, Lincoln Park in Chicago's North Side, has a conservatory, theater, museums, lily pool, nature sanctuary, archery range and rowing canal as well as playgrounds, beaches and noteworthy statues. Best of all, it also has a free 35-acre zoo boasting lions, tigers, bears and rhinos to start.
For more, 25-acre Millennium Park has free symphony rehearsals at Pritzker Pavilion and a wintertime ice rink while 300-acre Grant Park has Buckingham Fountain and the Field Museum.
For dog-friendly, try West Side's Wicker Park. Don't forget, either, that Chicago is along Lake Michigan; summer months are for sun, sand, "surf" and beach fun.
For history and culture, try the limestone-castle Chicago Water Tower, one of the few buildings to survive the Great Chicago Fire, and its City Gallery. The Chicago Cultural Center, originally the library, hosts world-class art exhibits beneath spectacular stained-glass domes.
The neoclassical Harold Washington Library Center at State Street and Congress Parkway is the largest library in the world; it's a great place to browse, let the kids "just be," and enjoy free Wi-Fi.
Wasting Time And Money
For vertigo junkies, entry to the Willis Building's Skydeck and Ledge costs adults $22 plus $14 per child. A Fast Pass with a 2- to 4-elevator wait runs $49 a person, and an Early Bird Admission is $65. The Day/Night Admission offers 2 visits for $33 per adult ($21 per child) but you'll wait twice, too;
It's worth it for architecture buffs, but pay in advance and time your visits, as peak-time lines can easily claim 3 hours.
In summer, Navy Pier is a bustling dining, shopping and entertainment destination, but the Windy City can become the "Bitterly Cold and Snowy City" - think wintertime versus summertime boardwalk.
However, the Smith Museum of Stained Glass Windows "in an 800 foot long series of galleries along the lower level terraces of Festival Hall" has 150 stained-glass windows of all types and themes on permanent display, making it a definite pier must-see freebie.