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Blow into the Windy City with These Chicago Travel & Entertainment Deals

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Chicago is a favorite vacation destination for many because it has the glamour and attractions of a large metropolis and that friendly, down-to-earth Midwest vibe. There’s something for everyone in Chicago — theater shows, cool music venues, and countless dining options, whether you’d like to try dishes from famous chefs or you want a classic Chicago hot dog and deep-dish pizza (no matter what Jon Stewart says). So pack your bags! We're going to Chi-town.

Getting There by Air

You'll want to carry on your suitcase full of money after taking advantage of United Airlines roundtrip fares to Chicago, where a seat aboard this short flight will cost you less than $200 there and back (from $157.80, a low by $14; expires December 31). Find low rates from Cleveland, Portland, Boston and Las Vegas to Chicago O’Hare International Airport then get ready to hop on the Blue line.

Places to Stay

If you're in Chicago for just a day, that's a shame! But you may find that a room at the Sheraton Chicago O'Hare Airport Hotel (from $99, a low by $30; expires December 31) is a great residence. The hotel not only offers complimentary shuttles to the airport, but your stay also includes daily breakfast.

Otherwise, grab your Ventra CTA card and check out a hip, new Joie de Vivre hotel and stay at the Hotel Lincoln (from $89, a low by $40; expires December 23). Located in the heart of the Lincoln Park neighborhood, you can take in the spectacular skyline and Lake Michigan atop the hotel at the J. Parker room and sip signature cocktails and share small plates created by award-winning chef Paul Virant while doing so.

Just a block from Magnificent Mile, another brand new hotel can greet you with welcoming arms: the chic Ivy Boutique Hotel offers stays in a king suite (from $109, a low by $70; expires December 31) for just pennies. You may not want to leave your room, what with its soaking tub and free WiFi, but your stay at this swanky hotel also includes two complimentary cocktails at the Devine lobby lounge, which is known for its delicious, nitrogen-infused drinks. Bottoms up!

Things to Do

Once you're good and ready to make your way through the windy streets of Chi, step out into the city and get exploring! Grab a 1-Day Go Chicago Tourism Pass ($70, a low by $5; expires March 31) and you can hit up 26 destinations, including the Chicago History Museum, Frank Lloyd Wright Home and Studio, and Museum of Science and Industry. Skip the lines for exclusive access to the Shedd Aquarium, the Field Museum, an Architecture River Cruise, and the Skydeck Chicago at the Willis Tower, where you can step out onto a glass ledge 1,353 feet above the city.

If the weather is blustery, you can spend some more time indoors at a cool and somewhat creepy museum in the Lincoln Park neighborhood. From unusual artifacts to the original plaster cast of the death mask of Napoleon, you won’t want to miss out on admission for two to the International Museum of Surgical Science (from $15, a low by $15; expires April 4), either. This pass allows two adults to explore the art and scientific exhibitions housed within a lakeside mansion-turned museum.

For the thrill seeker who has always thought he could win the Indy 500, a NASCAR race car ride (from $64, a low by $66; expires November 15, 2015) may be right up your alley. You'll reach top speeds for 3 laps as a passenger with a professional instructor on the Chicagoland Speedway. Or channel your inner Jeff Gordon and drive the Indy-style or NASCAR race car yourself (from $199, a low by $201) during a 5-minute timed drive that also includes a meeting with the crew chief, a driver’s fee, training, instruction, racing equipment, in-car radio communication with your spotter, and a graduate certificate.

After racing around town and the speedway, it's time to indulge in the other end of the spectrum with a relaxing spa package. First up is half-off a $200 credit to Bliss Spa (from $99, a low by $101; expires March 31), where you can choose from 12 massages, 16 facials and 12 nail services. This relaxing spot located in the W Chicago-Lakeshore hotel, which happens to have a delicious, signature brownie bar.

Alternatively, you can trade a sugar rush for a glass of bubbly during a massage and facial at the Spa at Four Seasons (from $199, a low by $120; expires March 31). Relax in style at this, one of four, AAA 5-Diamond properties in Chicago with a 55-minute massage and a 50-minute facial.

If you’d like to get pampered with a plus one, then book a couples massage at Savon Spa (from $99, a low by $150; expires February 28). Enjoy one complimentary mimosa each after a 60-minute Swedish massage in a couple’s room and relax into your Chicago vacation.

Once you and your other half are beautified and properly spoiled, it’s time to hit the town for dinner and drinks in style. Get started with wine flights for two at BIN 36 ($29, a low by $29; expires April 4). Called a “gourmet’s paradise” by the Michelin Guide, BIN 36 offers flights of Spanish wines, California selections, and Pinot Noirs, which also happen to pair well with the included cheese and charcuterie board served with crostini, apple, and a fig/honey compote.

For a luxe meal along the Magnificent Mile, grab a table and prepare for a steak dinner for two at Stetsons Modern Steak + Sushi (from $75, a low by $75; expires May 11). Dinner at this non-traditional steakhouse includes two glasses of wine from the restaurant’s award-winning list, an appetizer to share (such as the grilled calamari or octopus), and two entrees, of which every cut of the USDA prime beef is raised sustainably within 250 miles of Chicago. Dining with friends? Make a reservation for a steak dinner for four (from $149, a low by $151; expires May 11) and bon appétit!

For a quieter, elegant meal, grab your plus one and have dinner at the deca Restaurant + Bar at the Ritz-Carlton (from $75, a low by $42; expires March 31). The three-course dinner at this restaurant awarded the Bib Gourmand by the Michelin Guide includes two hors d’oeuvres (such as chicken liver and foie gras mousse), two entrees, and a shared dessert of 10-layer chocolate cake or another decadent selection. You’ll also receive 25 percent off pre- or post-dinner cocktails in the restaurant lounge. It's the perfect end to a great Chicago stay!

We hope we’ve inspired you to jet off to the Windy City for sightseeing, adventure, and relaxation. But if your travel plans include other destinations in the U.S. or around the globe, have a look at our weekly roundup of the best travel deals for additional discounted flights, hotels, and vacation packages.

At the time of publication, these travel deals offered the lowest prices we could find. Deals may include blackout dates, additional taxes, and fees. Some of our prices may be based on mandatory double occupancy.

Chicago Travel Deals

Contributing Writer

Josie Rubio is a Brooklyn, New York-based freelance editor and writer. She has visited five continents so far and loves to write about travel, food, nutrition, health... and pretty much everything. Follow her on Twitter at @JosieRubio.
Please note that, although prices sometimes fluctuate or expire unexpectedly, all products and deals mentioned in this feature were available at the lowest total price we could find at the time of publication (unless otherwise specified).
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