Cheap Chicago Weekend Getaways | Midwest Living

Cheap Chicago Weekend Getaways

A Chicago weekend for $500? You can drop that much just on hotels—or you can follow our advice for a bargain getaway to Chicago.
  • A bargain getaway

    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).

  • Hannah's plan-ahead sightseeing

    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.

  • Hannah's cheap travel tips: food

    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).

  • Hannah's cheap travel tips: activities

    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.

  • Sara's get-up-and-go weekend

    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.

  • Sara's cheap travel tips: food and lodging

    Grab a deal: Sites such as and 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.

  • Sara's cheap travel tips: activities

    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.

  • So what did we spend?

    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.

  • Planning for a bargain trip

    Where to start: For general information, contact Chicago's tourism office (877) 244-2246;, or the Chicago Convention and Visitors Bureau (312) 567-8500;

    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;

    For travel to the suburbs, use the Chicago Metra Railroad. (312) 322-6777;

    Pictured: Millennium Park's Cloud Gate, known as "The Bean."

  • Hannah's weekend: Where to eat and stay

    Irazu Try Costa Rica's unofficial national breakfast, a rice and bean combo called gallo pinto. (773) 252-5687;

    Maza Restaurant First time for Middle-Eastern? Share the Maza Deluxe, a feast of 20 hot and cold appetizers. (773) 929-9600;

    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;

  • Hannah's weekend: What to do

    31st Street Beach Wile away an hour cloud-gazing at the surprisingly quiet beach. (312) 742-5121;

    Bike and Roll Chicago Remember to ask for a lock so you can stop and explore by foot. (312) 729-1000;

    John Hancock Observatory Get a bird's-eye view of Chicago. Admission charged. (888) 875-8439;

    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;

    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;

    Millennium Park This now-iconic sculpture park offers free concerts and downloadable tours. (312) 742-1168;

    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;

  • Sara's weekend: Where to eat and stay

    Corner Bakery Cafe Grab a panini at this popular chain with locations around town. (312) 645-6000;

    Crepe and Coffee Palace Build your own crepe at this tiny breakfast and lunch spot. (773) 404-1300;

    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;

    Rockit Bar and Grill Burgers gone gourmet, with locations in River North and Wrigleyville. (312) 645-6000;

    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;

    Hotel Sax This boutique hotel has a trendy, rock-star vibe. From $209. (877) 569-3742;

  • Sara's weekend: What to do

    Grant Park Check the park's schedule for festivals throughout the summer and fall. (312) 742-7529;

    Museum of Contemporary Art The MCA makes a good stop for Mag Mile shoppers. (312) 280-2660;

    Chicago Cultural Center (left) Stop in for free concerts and art exhibits. (312) 744-6630;

    Akira This affordable boutique has locations in Lincoln Park, Bucktown and the Loop. (773) 489-0818;

    Threadless This Lakeview T-shirt shop rotates arty designs every week. (773) 525-8640;

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