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

Homewood Suites Chicago Downtown

3 stars
4.4 / 5 115 reviews
Home sweet Homewood A hot breakfast. Free Wi-Fi throughout the space. Gathering with others over wine, beer and soda. These daily conveniences might be missed while on vacation, but are customary amenities at Homewood Suites Chicago Downtown. Within walking distance of the Magnificent Mile and downtown Chicago restaurants, bars and shops, the River North Hilton property prides itself on the extras--regardless of whether the trip is for business or leisure. Highlights Complimentary daily hot breakfast buffetComplimentary Wi-Fi throughout the hotelFree nightly reception with meal, beer, wine and sodaFree grocery shopping serviceKing suites with full kitchens Rooms If these weren't hotel rooms, they might pass as city condos. Each space boasts two rooms and a full kitchen that includes a two-burner stove, microwave, dishwasher and refrigerator--ideal for a family looking to save money on dining expenses or an executive on an business trip. A wall separates the living, dining and sleeping quarters to provide maximum comfort. A palette of amber, brown and burgundy warms rooms, while several wall hangings add local flavor with images of Chicago landmarks. Guests sleep on the signature, plush Homewood Sweet Dreams mattress. LCD TV, two phone lines with voicemail and complimentary local calls are standard amenities. Features Homewood Suites Chicago Downtown provides a laundry list of bonuses that come at no extra cost to visitors. Expect a daily hot breakfast buffet, Wi-Fi throughout the space, a nightly reception with meal, beer, wine and soda, free coffee, tea or hot cider in the lobby all day, a grocery shopping service and a business center. During downtime, guests head to the indoor pool and cardio center, which are blessed with panoramic views of the Chicago skyline. Transportation O'Hare International Airport (16 miles)Midway Airport (11 miles)Closest train stops: Blue Line (Clark/Lake to O'Hare) and Orange Line (State/Lake to Midway)McCormick Place Convention Center (11 minutes) Attractions Magnificent MileMuseum of Contemporary ArtNavy PierJohn Hancock CenterTribune TowerWrigley BuildingCivic Opera House Business More than 3,000 square feet of meeting spaceFree Wi-Fi throughout the hotelBusiness center with computer and printer
Value Free hot breakfast and high speed internet access
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $109

Embassy Suites Chicago - Downtown/Lakefront

3 stars
4.2 / 5 312 reviews
Welcome to our Embassy Suites Chicago - Downtown/Lakefront hotel. Enjoy the convenience of our downtown Chicago hotel near Navy Pier, Magnificent Mile, Chicago River and Chicago's finest attractions.Showcasing spectacular views of downtown Chicago, the Embassy Suites Chicago - Downtown/Lakefront hotel near Michigan Avenue features upscale sophistication and more space to unwind and be yourself. Enjoy a relaxing stay in one of our spacious 455 suites featuring a private bedroom, separate living area with sofa sleeper, two 37-inch televisions, a refrigerator and a microwave.Enjoy our nightly Manager’s Reception* in our bright and spacious open-air atrium featuring contemporary design, a 75 ft. long live eco wall and grand views of the city. Indulge in a complimentary cooked-to-order breakfast each morning.Host a special event or business meeting in our 20,000 sq. ft. of meeting space or celebrate a special occasion in the elegant Chicago River Ballroom. After an exciting day discovering Chicago, unwind at the heated indoor pool and whirlpool, relax in the sauna or rejuvenate in our well-equipped fitness center.*Service of alcohol subject to state and local laws. Must be of legal drinking ag
Value Free cooked-to-order breakfast, Evening Reception
Flight + Hotel
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Hotel only
Nightly rates from $139

Wyndham Grand Chicago Riverfront

3 stars
4.2 / 5 257 reviews
This Wyndham Grand Chicago Riverfront effortlessly blends attentive service with chic accommodations for an oasis of comfort and style in the heart of vibrant downtown Chicago. Just steps from The Loop, the cultural district and several renowned business addresses, and convenient to both major airports, this hotel has breathtaking views of the Chicago River and is close to dining, shopping and landmark attractions. Stay connected to colleagues and loved ones with complimentary wireless Internet throughout the hotel. A 24-hour business center lets you take care of work any time, and a 24-hour fitness center lets you stay active. Two onsite restaurants serve all meals as well as room service. Events at this hotel are really special, with a dedicated staff and over 16,000 square feet of sophisticated, customized space including a penthouse ballroom with sweeping views. Oversized guest rooms feature MP3 dock, pillow-top mattress and work area. Pets are welcome. Valet parking is available for 61 USD per night with in/out privileges.
Value Save 10% on your stay
Flight + Hotel
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Hotel only
Nightly rates from $129

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.
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $129

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!
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $131
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Sat, Apr 11 - Tue, Apr 14 $97
Los Angeles Chicago Thu, Apr 16 - Mon, Apr 27 $158
Washington DC Chicago Wed, Apr 1 - Wed, Apr 8 $145
San Francisco Chicago Tue, Mar 31 - Mon, Apr 6 $268
Newark Chicago Tue, Mar 17 - Wed, Mar 18 $188
Atlanta Chicago Tue, Mar 31 - Tue, Apr 7 $107
Seattle Chicago Tue, Mar 31 - Sat, Apr 4 $262
Boston Chicago Sat, Apr 4 - Tue, Apr 7 $161
Dallas Chicago Tue, Apr 7 - Tue, Apr 21 $81
Denver Chicago Wed, Mar 18 - Tue, Mar 31 $97
Phoenix Chicago Wed, Apr 15 - Tue, Apr 21 $98
Orlando Chicago Thu, Mar 19 - Tue, Mar 24 $185
San Juan Chicago Wed, Apr 22 - Wed, May 6 $338
Mexico City Chicago Thu, Apr 9 - Thu, Apr 16 $364
Philadelphia Chicago Mon, Mar 16 - Mon, Mar 23 $138
San Diego Chicago Fri, Apr 24 - Wed, May 6 $227
Fort Lauderdale Chicago Wed, Apr 22 - Fri, Apr 24 $199
Las Vegas Chicago Sat, Mar 7 - Tue, Mar 10 $222
Guadalajara Chicago Fri, Mar 6 - Fri, Mar 13 $427
Tampa Chicago Thu, Mar 19 - Tue, Mar 24 $162
Houston Chicago Mon, Apr 20 - Tue, Apr 21 $120
Baltimore Chicago Sat, Mar 7 - Sat, Mar 14 $187
Honolulu Chicago Sun, Apr 26 - Sun, May 10 $711
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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