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

Congress Plaza Hotel at Grant Park

3 stars
3.4 / 5 1507 reviews
With its neon-red sign standing out against the Chicago skyline, its vaulted Italianate ceilings, and glimmering 'Gold Room' banquet hall, the Congress Plaza Hotel makes an imposing first impression. Once known as the "Home of Presidents" due to its popularity with both Roosevelt's, Woodrow Wilson and Richard Nixon, it's been operating since 1893. Valet dry-cleaning and barber services of yesteryear sit side-by-side with modern amenities like audiovisual tech for business meetings and a 24-hour fitness center. On-site eating options are globally diverse (Rafael's Steakhouse) and come straight from the griddle in the morning (Gazebo Restaurant). In the evenings, settle into a leather back armchair with a bourbon, or take your shots at the dartboard in the Congress Lounge, where both business users and vacationers gather for some much-needed R&R. Key facts871 guestrooms36 suites23 meeting/event rooms2 restaurants: Rafael's Steakhouse, Gazebo RestaurantCongress Lounge & BarGift shopBarber shop24-hour gymValet dry cleaning/shoeshineSmoking rooms available on request NeighborhoodAcross the street from Grant Park and the famous Buckingham Fountain, Congress Plaza rests on the main thoroughfare and shopping mecca of Michigan Avenue, aka, the Magnificent Mile. The hotel is walking distance from world-renowned institutions like the Art Institute of Chicago, Shedd Aquarium, and the fascinating Field Museum. Found on the banks of Lake Michigan, the Field Museum is the home of "Sue," the largest and most complete Tyrannosaurus Rex skeleton ever discovered, as well as a life-size Maori meeting house. Hints and tipsThe Congress is frequently nicknamed 'the most haunted hotel in Chicago,' and budding paranormal detectives should request a room in the oldest part of the building, the South Tower, for the 'highest chance' of ghostly activity.Be on the lookout for characters like notorious murder victim Peg Leg Johnny, or test your courage near the 12th floor room which was allegedly closed down due to paranormal activity.
Value Save 10% on your stay
Flight + Hotel
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Hotel only
Nightly rates from $125

Inn of Chicago, an Ascend Collection hotel

3 stars
3.4 / 5 255 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, the Inn of Chicago 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 high-speed wireless Internet accessComplimentary stay for children under 18The 22nd floor Skyline Terrace RoomsThe rooms and suites at the Inn of Chicago 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. 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. FeaturesGreat city views might well be the most valuable cache for Chicago hotels and for the Inn of Chicago, 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 Complimentary wireless Internet access 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 $123

Club Quarters Central Loop

3 stars
4.1 / 5 822 reviews
Business traveler headquarters in Chicago's LoopThe Club Quarters Central Loop hotel might be mistaken for an office building with its subdued presence. A black awning marks this discrete spot and lends a sense of privacy. The hotel targets business travelers whose work brings them to the financial district and plays host to leisure travelers who want easy access to downtown attractions. Guests find great value for the location, price and attentive service, including a 24-hour concierge. The Club Quarters Central Loop hotel is within walking distance of several of Chicago's major attractions. Highlights Minutes from Michigan Avenue 24-hour concierge service Free high-speed wireless Internet throughout the hotel Elephant & Castle Pub and Restaurant next door RoomsThe clean and comfortable rooms at the Club Quarters Central Loop hotel keep the professional’s needs in mind. Ergonomic chairs and task lighting ease late work nights, while pillow-top mattress dressed in premium linens promise a refreshing night of sleep. Bookshelves display dictionaries and almanacs for a welcome scholarly touch. All rooms have complimentary wireless Internet access. FeaturesThe amenities at the Club Quarters Central Loop hotel are designed to keep guests productive. Find free high-speed wireless Internet access throughout the hotel, free use of a computer and printer, and five meeting rooms. Travelers looking to relax visit the restaurant and bar next door, exercise in the fitness room or lounge in the Private Club Room (Club Quarters members only) with complimentary coffee, tea, newspapers, magazines and games.Free, chilled bottled water is available on each floor. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (8.9 mi/14.3 km) Blue Line (Jackson/Dearborn) (0.1 mi/0.2 km) Orange Line (Quincy/Wells) (0.1 mi/0.2 km) McCormick Place Convention Center (2.1 mi/3.3 km) Attractions Board of Trade (0.1 mi/0.2 km) Theater district (0.2 mi/0.3 km) Willis (formerly Sears) Tower (0.2 mi/0.4 km) Symphony Center (0.3 mi/0.5 km) Chicago Mercantile Exchange (0.3 mi/0.5 km) The Art Institute of Chicago (0.4 mi/0.6 km)
Flight + Hotel
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Nightly rates from $98

Embassy Suites Chicago - Downtown/Lakefront

3 stars
4.1 / 5 445 reviews
All-suite hotel by Navy Pier and other Chicago attractionsThe Embassy Suites Chicago - Downtown/Lakefront hotel boasts an envious Chicago address, just two blocks from Navy Pier and a short walk to the Magnificent Mile. Peer out of one of the two-room suites to Chicago’s most recognizable landmarks. Business, shopping and entertainment districts are minutes away. Contemporary styling, complimentary cooked-to-order breakfast and weeknight manager receptions keep guests comfortable and well fed. A movie theater and restaurant in the building also make rainy days feel like more of a good thing. Highlights Two blocks to Navy Pier, close to the Magnificent Mile Spacious two-room suites Complimentary cooked-to-order breakfast 24-hour fitness center and heated indoor pool RoomsA dedicated living room in the two-room suites affords business travelers a separate space for work or families an additional room for children to rest on a sleeper sofa. The private bedrooms at the Embassy Suites Chicago - Downtown/Lakefront hotel are styled with contemporary furniture, fine linens and one king or two double beds. A palette of browns, square-patterned carpeting and soft lighting work together to create a space that is warm and familiar. Every suite features a flat-screen plasma TV, wet bar, refrigerator, microwave and high-speed Internet access (fees apply). FeaturesGuests of the Embassy Suites Chicago - Downtown/Lakefront hotel enjoy a free cooked-to-order breakfast served each morning inside an open, light-filled atrium. Every evening, the manager hosts a reception in the Sky Lobby. For the rest of the day, count on P.J. Clarke’s on the first floor of the property for favorite American eats, like burgers, meatloaf, salads and desserts.Guests exercise at the 24-hour fitness center or swim in the heated, indoor pool.High-speed Internet access is available throughout the hotel, including the 24-hour business center (fees apply). On-site indoor valet and self-parking is available for a fee. Transportation O’Hare International Airport (15.8 mi/25.4 km) Midway Airport (9.9 mi/15.9 km) Blue Line (Grand) (1.4 mi/2.3 km) Orange Line (State/Lake) (0.6 mi/0.9 km) McCormick Place Convention Center (2.8 mi/4.4 km) Nearby attractions Navy Pier (0.8 mi/1.3 km) Lake Michigan (0.8 mi/1.3 km) The Magnificent Mile (0.7 mi/1.1 km) Millennium Park (0.3 mi/0.4 km) Grant Park (0.3 mi/0.4 km) John Hancock Center (0.5 mi/0.9 km) Water Tower Place (0.5 mi/0.8 km) Business 24-hour business center with complimentary Internet access20,000 square feet of function space, including 16 meeting rooms Chicago River Ballroom with room for up to 500 guests Video, sound and lighting technology available Full-service catering and convention staff
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Nightly rates from $179

The Talbott Hotel

4 stars
4.6 / 5 1473 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 by Orbitz in 2012, the Talbott features exclusive touches like the creative Tippling Brothers cocktail menu at the Little Market Brasserie, 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: Little Market Brasserie 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.
Value Last Minute Deal!
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Nightly rates from $185
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Wed, Sep 3 - Tue, Sep 9 $205
Los Angeles Chicago Sat, Sep 20 - Tue, Sep 23 $266
Washington DC Chicago Mon, Sep 15 - Thu, Sep 18 $105
San Francisco Chicago Thu, Sep 11 - Tue, Sep 16 $245
Newark Chicago Wed, Sep 10 - Thu, Sep 11 $248
Atlanta Chicago Tue, Sep 9 - Tue, Sep 16 $262
Seattle Chicago Sat, Sep 6 - Tue, Sep 9 $299
Boston Chicago Wed, Sep 10 - Tue, Sep 16 $165
Dallas Chicago Wed, Sep 3 - Wed, Sep 10 $165
Denver Chicago Sat, Sep 13 - Wed, Sep 17 $145
Phoenix Chicago Sat, Sep 6 - Wed, Sep 10 $238
Orlando Chicago Wed, Aug 27 - Mon, Sep 8 $205
San Juan Chicago Wed, Sep 17 - Tue, Sep 23 $281
Mexico City Chicago Sat, Sep 6 - Sun, Sep 28 $401
Philadelphia Chicago Thu, Sep 18 - Wed, Sep 24 $299
San Diego Chicago Thu, Sep 18 - Wed, Sep 24 $271
Fort Lauderdale Chicago Wed, Sep 3 - Tue, Sep 9 $225
Las Vegas Chicago Tue, Sep 9 - Sat, Sep 13 $258
Guadalajara Chicago Sun, Aug 31 - Sun, Sep 7 $367
Tampa Chicago Wed, Aug 20 - Mon, Aug 25 $255
Houston Chicago Tue, Sep 9 - Wed, Sep 10 $193
Baltimore Chicago Tue, Sep 9 - Sat, Sep 13 $175
Honolulu Chicago Thu, Sep 11 - Thu, Sep 18 $727
Orange County Chicago Fri, Sep 5 - Wed, Sep 10 $266
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Best time to take a vacation to Chicago

  • 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.

Insider tips for Chicago travel

  • 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

  • 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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