Cheap Chicago Vacations

Chicago

Your Chicago vacation

From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.

Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.

Cheap Vacation Packages

Cheap Chicago Vacation Packages

Inn of Chicago, an Ascend Collection hotel

3 stars
3.4 / 5 260 reviews
Contemporary style, European charm in ChicagoIn the Roaring '20s, this boutique Streeterville hotel hosted celebrities and showgirls. While those times have faded, the air of glamour remains at the Inn of Chicago, an Ascend Collection hotel. For proof, just stroll the lobby, where zebra ottomans, fresh-cut orchids and metallic embossed walls create drama and urban appeal. With its central location and focus on value, Inn of Chicago, an Ascend Collection hotel is a gem for business or leisure travelers seeking convenient access to the Magnificent Mile and its many diversions. Highlights Prime Chicago location just east of Magnificent MileFree wireless Internet access in the lobbyComplimentary stay for children under 18The 22nd floor Skyline Terrace RoomsThe rooms and suites at Inn of Chicago, an Ascend Collection hotel feel more like apartments than hotel rooms, and that's on purpose. Back in the 1920s, the former Hotel St. Clair offered one-bedroom apartments, and the effects linger today at the Inn of Chicago, an Ascend Collection hotel. Space for entertaining, working and lounging are separate from the sleeping area. Big picture windows with skyline views, photos of Chicago, zebra upholstery and unique layouts lend to a chic city vibe. In-room wireless Internet access is available for a fee. FeaturesGreat city views might well be the most valuable cache for Chicago hotels and for Inn of Chicago, an Ascend Collection hotel, this view comes at the Skyline Terrace on the 22nd floor. The Sky Suites also provide lofty views, while a dedicated party space accommodates up to 100 guests for weddings and other social events. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (9.8 mi/15.9 km) Blue Line (Grand) (1.7mi/2.7 km) Orange Line (State/Lake) (0.5 mi/0.9 km) McCormick Place Convention Center (2.9 mi/4.6 km) Attractions The Magnificent Mile (0.1 mi/0.1 km) Water Tower Place (0.4 mi/0.6 km) Navy Pier (1 mi/1.6 km) Lake Michigan (0.2 mi/0.3 km) Millennium Park (0.7 mi/1.1 km) Business Business center work station 5 meeting rooms 5,500 square feet of function space for up to 125 guests Concierge services Policies and fees NOTE: Parking fees are as follows: $48 for self-parking and $52 for valet parking with unlimited in/out privileges.
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Nightly rates from $71

The Silversmith Hotel Chicago

3 stars
4.2 / 5 238 reviews
Landmark in the Loop near attractions and shoppingIt's only fitting that this historic hotel is just a few blocks from Jewelers Row given its name and former purpose. In the 1890s, its tenants worked in the jewelry and silver trade. Today, landmark elements -- a cast iron staircase, terra cotta touches -- give the Silversmith Hotel Chicago a unique architectural identity. Ideally situated near the Magnificent Mile and Millennium Park, the Silversmith Hotel Chicago appeals to budget-minded travelers seeking quick access to Chicago's most popular attractions. Highlights One block to the Magnificent Mile, Millennium Park and State Street shopping24-hour fitness centerFree high-speed Internet access throughout the hotelDining at Ada's Deli & Restaurant and cocktails at the 14 Karat LoungeHistoric, independent hotel with Arts and Crafts style RoomsRooms and suites at the Silversmith Hotel Chicago serve their purpose, providing comfortable beds and a place to freshen up in between sightseeing excursions. The hotel’s 12-foot ceilings add dimension, while 10-foot picture windows view the city and the El. Wood headboards, desks and Prairie-style lamps complete the casual look. Complimentary wireless Internet access is available throughout the property. FeaturesIntimate and under the radar, the Silversmith Hotel Chicago does not fit the trendy boutique mold, but guests will appreciate its location. No less than a dozen attractions are within walking distance, including the theater district, Jewelers Row, State Street, Grant Park and Millennium Park. Transportation O'Hare International Airport (15.8 mi/25.4 km)Chicago Midway Airport (9.2 mi/17.8 km)Blue Line (Monroe/Dearborn to O'Hare) (0.2 mi/0.3 km)Orange Line (Madison/Wabash to Midway) (0.1 mi/0.1 km)McCormick Place Convention Center (2.1 mi/3.5 km) Attractions Jewelers Row (0.1 mi/0.1 km)The Art Institute of Chicago (0.1 mi/0.1 km)Millennium Park (0.3 mi/0.4 km)Grant Park (0.4 mi/0.6 km)State Street (0.6 mi/0.9 km)Field Museum (1.2 mi/1.9 km)Shedd Aquarium (1.2 mi/1.9 km)Adler Planetarium (1.5 mi/2.3 km) Business Executive boardroom hosts up to 12 guestsChicago Landmark Room hosts up to 120 guestsPresentation equipment available, including 34-mm slide projector, flip chart and markers, LCD projector, microphone, VCR, overhead projector, modem lines and white boardsBusiness centerFree high-speed Internet access available throughout the Silversmith Hotel Chicago
Value Business Advantage - Arrival Day Cancel
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Nightly rates from $105

Hotel Rush

3 stars
4.1 / 5 176 reviews
Access to attractions, plus free Wi-Fi and indoor poolGuests at the Hotel Rush enjoy a plum location just off the Magnificent Mile. Whether the agenda is hitting downtown shops, restaurants, bars or landmarks, leisure travelers will find no shortage of distractions nearby while executives enjoy convenient access to the Loop and the Financial District. With standard amenities like complimentary Wi-Fi throughout the property, an indoor pool and fitness and business centers, the property stands as a well-rounded option for budget-minded vacationers. Highlights Close to the Magnificent MileComplimentary Wi-Fi throughout the propertyIndoor pool24-hour business centerSushi restaurant and artisan breakfast and lunch eatery onsite RoomsSmoke-free rooms at the Hotel Rush are airy and open with windows that look out to the city. Plump duvets boast a subtle beige plaid print that matches extra seating, curtains and artwork around the room. In every space, expect complimentary Wi-Fi or hardwired access, plus extras such as refrigerator, microwave, desk and free bottled water. For extra comfort, visitors can request a room with a balcony, whirlpool or wet bar. FeaturesVirtual office. Night on the town. Quick lunch. Energizing workout. Hotel Rush answers all these needs. A 24-hour business center is open for checking email, printing an agenda or sending an important document via fax. Craving a healthy snack before hitting the Magnificent Mile? Try e.leaven Food Company for artisan pastries, omelets, salads and sandwiches. For people-watching, head to Sushi Taiyo, where inventive rolls complement rice and noodle dishes. Guests whose routine requires a daily dose of cardio can work out in the 24-hour fitness center equipped with Life Fitness machines or swim laps in the indoor pool with skylights and windowed views of the city. Transportation O'Hare International Airport (17 miles)Midway Airport (13 miles)Closest train stops: Blue Line (Chicago to O'Hare) and Orange Line (Roosevelt to Midway)McCormick Place Convention Center (10 minutes) Attractions Magnificent MileRush StreetGold CoastMillennium ParkGrant ParkJohn Hancock CenterNavy Pier Business 4,000 square feet of meeting spaceCatering by Lawry's Prime Rib, e.leaven Food Company and Sushi Taiyo24-hour business centerComplimentary high-speed wired and wireless Internet access Terrace available for seasonal events Policies and feesThe lobby will undergo refurbishments from 19 January until 20 March 2015.
Value Stay 2 nights, Save 10%
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Nightly rates from $110

The Talbott Hotel

4 stars
4.6 / 5 1277 reviews
Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the vintage-style boardrooms feature 1920s mahogany walls. Awarded the Best in Stay Award in 2014 - 2015, the Talbott features exclusive touches like the creative Tippling Brothers cocktail menu at the Mercadito Fish Co., and the knowledgeable 'Concierge Blog' on the hotel's site, setting the hotel far apart from other Chicago accommodations. Key facts149 guestroomsPets allowed (up to 50 pounds, and fees may apply)Conference and event spaces: 3 rooms, up to 200 guestsFitness centerLaundry serviceFree Wi-Fi Restaurant/bar: Mercadito Fish Co. NeighborhoodWith a prime location just a few blocks from Washington Square Park, Oak Street and the Magnificent Mile, The Talbott Hotel comes with easy access to shops like Bloomingdale's and Macy's, as well as the scenic Lakefront Trail on the shores of Lake Michigan. The Art Institute of Chicago is less than two miles from The Talbott's front entrance, boasting a staggering collection of over 250,000 works of art, including work by Vincent van Gogh, Claude Monet and Mary Cassatt. Hints and tipsFor privileged views of Chicago and a bit of distance from busy Delaware Street, ask for a room on the upper floors.For a more personalized stay, the Talbott Hotel's packages offer everything from the princess treatment for young daughters - including milk and cupcakes at turndown - to a $50 gift certificate  for the 900 North Michigan Shops. Policies and feesGuests must be at least 21 years of age to check in.
Value Last Minute Deal!
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Nightly rates from $131

The Godfrey Hotel Chicago

4 stars
4.4 / 5 117 reviews
Godfrey means peace and welcome; welcome to The Godfrey Hotel Chicago. The Godfrey Hotel Chicago offers unforgettable style from the Cubist-influenced facade to the chic accommodations, each detail of this striking new hotel has been designed with the guest's experience in mind.
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Nightly rates from $129
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Tue, Mar 10 - Tue, Mar 24 $97
Los Angeles Chicago Thu, Apr 16 - Mon, Apr 27 $158
Washington DC Chicago Mon, Apr 27 - Wed, Apr 29 $145
San Francisco Chicago Wed, Apr 29 - Tue, May 5 $205
Newark Chicago Thu, Apr 16 - Fri, Apr 17 $177
Atlanta Chicago Thu, Apr 16 - Tue, Apr 21 $98
Seattle Chicago Mon, Mar 16 - Wed, Mar 18 $264
Boston Chicago Sat, Apr 25 - Tue, Apr 28 $137
Dallas Chicago Tue, Mar 24 - Wed, Apr 8 $81
Denver Chicago Wed, Apr 15 - Wed, Apr 22 $97
Phoenix Chicago Wed, Apr 15 - Tue, Apr 21 $98
Orlando Chicago Tue, Mar 17 - Tue, Mar 24 $194
San Juan Chicago Tue, Apr 14 - Tue, May 12 $363
Mexico City Chicago Thu, Apr 23 - Thu, Apr 30 $351
Philadelphia Chicago Sat, Apr 18 - Tue, Apr 21 $98
San Diego Chicago Fri, Apr 24 - Wed, May 6 $227
Fort Lauderdale Chicago Wed, Apr 22 - Sun, Apr 26 $177
Las Vegas Chicago Wed, Apr 1 - Wed, Apr 8 $168
Guadalajara Chicago Wed, Apr 15 - Sun, Apr 19 $369
Tampa Chicago Wed, Apr 15 - Mon, Apr 20 $145
Houston Chicago Wed, Apr 8 - Mon, Apr 13 $99
Baltimore Chicago Tue, Apr 14 - Tue, Apr 21 $157
Honolulu Chicago Wed, Mar 18 - Mon, Mar 23 $697
Orange County Chicago Wed, Apr 8 - Tue, Apr 14 $295
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  • If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.

  • Pancho Pistolas

    Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

  • Ping Tom Memorial Park

    Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

  • Montrose Harbor

    Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

  • Alta Vista Terrace

    Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

  • Cafe Selmarie

    Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

  • Chicago highlights
  • Navy Pier

    For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.

  • Magnificent Mile

    The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.

  • Lincoln Park Zoo

    For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.

  • Cultural Chicago

    If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.

  • Millennium Park

    Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.

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