Our mission: a weekend for two in Chicago for $500. Whether you like to plan ahead or get up and go at the last minute, you'll love our wallet-friendly (and fun!) tips for a Windy City getaway. Check out the plan-ahead ideas from Midwest Living® editor Hannah Agran (at left side of photo) and the grab-a-deal tips from her colleague Sara Reimer (at right side of photo).
As a travel editor, I have a flexible schedule, but my husband, Juan, isn't so lucky. We always plan vacations in advance. Here's what my planning saved us for Chicago:
-- Hotel: I quickly learned that even booking early at a downtown Chicago hotel would blow our budget. So I looked to the suburbs, where an affordable chain hotel, the Renaissance Chicago North Shore, put us a 45-minute train ride from the city.
-- Transportation: I was nervous about cab fares. Checking maps first, I picked places we could hit by foot -- or by bike! I even saved $5 reserving our wheels online.
Pictured: I chose the cheapest bike -- the retro Beach Cruiser -- for our ride.
Eat breakfast at a coffee shop. The first morning, we ate at the hotel, a $30 beginner's mistake that pushed the day's food budget over $100. The next day, we stopped at Starbucks -- leaving us with more cash (and less guilt) for an alfresco lunch at Tempo Cafe (left), near the Magnificent Mile.
Try ethnic restaurants, where you can explore new flavors without spending a bundle. We munched on fried plantains and drank colorful milk-and-fruit smoothies called batidos at Irazu, a Costa Rican restaurant in artsy Bucktown. Later, I introduced Juan to lamb kabobs and hummus at Maza Restaurant, a white-tablecloth find with not-quite-white-tablecloth prices in Lincoln Park.
Avoid pesky small expenses. Knowing we'd have backpacks on our bike ride, we filled our own bottles at the lakeshore trail water fountains. We also packed granola bars for snacks (and brought cash to avoid ATM fees).
Choose close-together activities that will stretch your dollar. We dropped $47 for bike rentals, but that gave us a cheap, fun way to zip along the lakeshore, checking the 31st Street Beach, Navy Pier and the Lincoln Park Zoo (all free!) off our list. And, since the bikes came with locks, we could stop and sightsee -- or join families wading in Millennium Park's Crown Fountain (left).
Go where the crowds don't. Pre-trip research clued me in to the little-known Bridgehouse Museum, where, for just $3 apiece, we saw the massive gears that lift the Michigan Avenue bridge, and we learned all about the Chicago River. Visiting that hidden gem freed up the last of our $500 for two not-so-cheap rides up the Hancock Tower for Juan's first bird's-eye view of Chicago.
I'm always game for an impromptu road trip to Chicago. Usually, I travel on the cheap: split the cost of gas, crash on a friend's couch, dine on deep-dish pizza. This time, I wanted to do it up right -- without going broke.
I asked my friend Julie, another bargain-hunter, to go for a girls' weekend. Staying close to shops, museums and nightlife was a priority, so we checked travel websites for downtown hotel deals. When a great rate popped up, we snagged it and hit the road.
Pictured: A leisurely walk through the Lincoln Park neighborhood is fun -- and free.
Grab a deal: Sites such as Hotwire.com and Priceline.com offer 30 - 60 percent hotel discounts. The catch: You find out which hotel after you pay. Be flexible with dates for the best deals. The week we left, I nabbed a room at River North's stylish Hotel Sax.
Buy cheap eats at a farmers market or festival. In the warm months, most neighborhoods host events with food vendors. Find one as you explore or check with your hotel. We loved the Green City Market (left) on the south edge of Lincoln Park for its sustainably grown, fresh foods. Quick bites, such as bacon-cheddar quiche, buckwheat crepes and burgers ($3 - $10), make a bargain lunch.
Hit a BYOB eatery to lower your bar tab. (Just make sure there's no corkage fee.) We picked up a $10 bottle of wine on our way to Lakeview's Tango Sur restaurant for giant slabs of juicy Argentine beef and crispy chicken-stuffed empanadas. Only drawback: The place was packed; we waited 45 minutes for a table.
Shop North Side neighborhoods. The Magnificent Mile is great for splurging but doesn't offer many steals, so Julie and I took the train to Lincoln Park to browse eclectic vintage shops and discount clothing boutiques. Best bet for the budget-minded fashionista: Chicago-based Akira (left), which sells runway-inspired dresses (from $20) and flirty accessories (from $10). I scored a $14 fitted tee.
Cash in on free tours. Many art museums offer free daily tours of featured exhibits, after you pay general admission. We took advantage of a 40-minute Jeff Koons tour at Chicago's Museum of Contemporary Art. Our guide explained how Koons' kitschy sculptures (stainless-steel balloon dogs and other everyday objects) are metaphors for American culture -- insights we might have missed otherwise.
Befriend your concierge. Ours gave great advice on affordable restaurants and free events, such as a dance festival in Grant Park, plus directions to nearby train stations. We tipped $10 to say thanks.
Hannah: I did it! With careful planning and a few sacrifices -- no ice cream cones, for instance -- my husband and I pulled off a Chicago weekend for two for less than $500 ($498, to be exact). Sure, a hotel in the 'burbs isn't as glamorous as a downtown high-rise, but we'll never forget riding the train into the city with hundreds of excited Cubs fans.
Sara: Julie and I didn't make our $500 goal (pricey hotel parking put us over to $587), but we learned budget lessons for next time. One to note: You can usually park several blocks away from your hotel for half the price. And our top freebie? The Chicago Cultural Center, home to lectures, art, concerts and the world's biggest stained-glass Tiffany dome.
Pictured: Gardens near the Lincoln Park Zoo.
Where to start: For general information, contact Chicago's tourism office (877) 244-2246; explorechicago.com , or the Chicago Convention and Visitors Bureau (312) 567-8500; choosechicago.com .
Getting around: Save money -- and get a better feel for the city -- by riding public transportation. Most maps show train and El lines, and signs at bus stops explain the routes. For extra ease, buy passes online. For travel within the city, contact the Chicago Transit Authority. (888) 968-7282; transitchicago.com 
For travel to the suburbs, use the Chicago Metra Railroad. (312) 322-6777; metrarail.com 
Pictured: Millennium Park's Cloud Gate, known as "The Bean."
Irazu Try Costa Rica's unofficial national breakfast, a rice and bean combo called gallo pinto. (773) 252-5687; irazuchicago.com 
Maza Restaurant First time for Middle-Eastern? Share the Maza Deluxe, a feast of 20 hot and cold appetizers. (773) 929-9600; mazachicago.com 
Tempo For less than $25, we got huge omelets, coffee, juice and a basket of Greek toast (left) at this 24-hour brunch spot just blocks from the Mag Mile. (312) 943-4373
Renaissance Chicago North Shore This chain hotel makes a great suburban base for exploring. From $99. (847) 498-6500; marriott.com 
31st Street Beach Wile away an hour cloud-gazing at the surprisingly quiet beach. (312) 742-5121; chicagoparkdistrict.com 
Bike and Roll Chicago Remember to ask for a lock so you can stop and explore by foot. (312) 729-1000; bikeandroll.com 
John Hancock Observatory Get a bird's-eye view of Chicago. Admission charged. (888) 875-8439; jhochicago.com 
Lincoln Park Zoo One minute you're walking through a park; the next, you're in a world-class zoo (left). Free. (312) 742-2000; lpzoo.org 
McCormick Bridgehouse and Chicago River Museum On select days, visitors can reserve a spot inside when the bridge lifts. Admission charged; open seasonally. (312) 977-0227; bridgehousemuseum.org 
Millennium Park This now-iconic sculpture park offers free concerts and downloadable tours. (312) 742-1168; millenniumpark.org 
Navy Pier This hub of lakefront activity includes a 90-foot Ferris wheel, restaurants, boat cruises and the free Smith Museum of Stained Glass. (800) 595-7437; navypier.com 
Corner Bakery Cafe Grab a panini at this popular chain with locations around town. (312) 645-6000; cornerbakerycafe.com 
Crepe and Coffee Palace Build your own crepe at this tiny breakfast and lunch spot. (773) 404-1300; icosiumkafechicago.com 
Green City Market Shop for veggies or grab a healthful breakfast or lunch. Open Wednesdays and Saturdays, 7 a.m. to 1 p.m. (773) 880-1266; greencitymarket.org 
Rockit Bar and Grill Burgers gone gourmet, with locations in River North and Wrigleyville. (312) 645-6000; rockitbarandgrill.com 
Tango Sur Best deal at this popular BYOB restaurant (left): a half-slab Argentine filet for two for a mere $29.50. (773) 477-5466; tangosur.net 
Hotel Sax This boutique hotel has a trendy, rock-star vibe. From $209. (877) 569-3742; hotelsaxchicago.com 
Grant Park Check the park's schedule for festivals throughout the summer and fall. (312) 742-7529; chicagoparkdistrict.com 
Museum of Contemporary Art The MCA makes a good stop for Mag Mile shoppers. (312) 280-2660; mcachicago.org 
Chicago Cultural Center (left) Stop in for free concerts and art exhibits. (312) 744-6630; cityofchicago.org 
Akira This affordable boutique has locations in Lincoln Park, Bucktown and the Loop. (773) 489-0818; shopakira.com 
Threadless This Lakeview T-shirt shop rotates arty designs every week. (773) 525-8640; threadless.com