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
3.3 / 5 240 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 $55

The Talbott Hotel

4 stars
4.6 / 5 1225 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 $116

The Godfrey Hotel Chicago

4 stars
4.4 / 5 85 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 $80

MileNorth, A Chicago Hotel

4 stars
4.2 / 5 417 reviews
This boutique property offers a residential-style retreat that soars above Chicago's Magnificent Mile. Each floor is home to no more than 11 spacious guest rooms and suites, and your evenings would be well spent enjoying appetizers and sipping cocktails at the 52EIGHTY rooftop lounge. MileNorth's accommodations are inspired by neoclassical, Art Deco and classical deco trends with light shades, huge windows, shimmering silver tones, and white glass doors all set against brash colors. Key facts215 guestrooms2 suites29 floorsBarista Bar52EIGHTY Rooftop LoungeCoffee shop24-hour fitness centerBallroomBanquet facilities3,000-square-feet of meeting space24-hour front deskPet-friendly (refer to company pet policy for further details, fees may apply)Smoke-free property NeighborhoodLocated one block east of famous Michigan Avenue, the excitement of the big city is just outside your door, and Chicago's Magnificent Mile is your boulevard to it all when you stay at the gracious MileNorth Hotel. The shores of Lake Michigan are due east, Neiman Marcus is just down the block, and the John Hancock Center beckons to the north. Live theater and entertainment at Navy Pier brings culture vultures of all stripes. Your favorite shopping fantasies come true up and down the Magnificent Mile, where you'll find the ultimate in luxury retail. Get closer to the stars with a visit to the John Hancock Observatory, and wear comfortable shoes, because the best of Chicago is all within walking distance of your MileNorth front door. Hints and tipsAsk the friendly staff for directions - whether you're organizing a tour of nearby museums, or setting up a business meeting, you can count on the hotel's premier concierge services. Policies and FeesOvernight valet parking fee is $57 USD.Guests must at least 21 years of age to check-in, and should present a valid photo ID.
Value Stay 1 night, save 10%
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Nightly rates from $95

Swissotel Chicago

4 stars
4.1 / 5 306 reviews
An all-glass triangular hotel, wedged into the confluence of the Chicago River and Lake Michigan, has spectacular wrap-around views from Navy Pier to Grant Park. Swissotel Chicago offers 661 air-conditioned, tastefully decorated and generously oversized rooms and suites. Relax above the city in our Penthouse Swimming Pool, Whirlpool and Health Club. Spa services available. Overnight parking charge will be $65.00/day with in and out privileges. Hybrid vehicles receive a 50% discount. A fee of $15.00 per room, per day (up to 4 guests) will apply for the use of the health club/swimming pool.
Value Book early and save 10% on your stay
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Hotel only
Nightly rates from $119
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Sat, Jan 10 - Sat, Jan 17 $137
Los Angeles Chicago Wed, Jan 14 - Sat, Jan 17 $237
Washington DC Chicago Fri, Jan 9 - Fri, Jan 16 $115
San Francisco Chicago Wed, Feb 4 - Sat, Feb 7 $246
Newark Chicago Sat, Jan 24 - Wed, Jan 28 $235
Atlanta Chicago Tue, Feb 3 - Sat, Feb 7 $117
Seattle Chicago Wed, Jan 21 - Tue, Jan 27 $278
Boston Chicago Wed, Jan 28 - Sat, Jan 31 $133
Dallas Chicago Sat, Jan 10 - Sat, Jan 17 $81
Denver Chicago Thu, Jan 15 - Tue, Jan 20 $81
Phoenix Chicago Sun, Feb 1 - Tue, Feb 3 $177
Orlando Chicago Wed, Jan 14 - Wed, Jan 21 $97
San Juan Chicago Tue, Jan 27 - Mon, Feb 2 $332
Mexico City Chicago Wed, Jan 14 - Thu, Jan 15 $362
Philadelphia Chicago Sun, Jan 18 - Mon, Jan 19 $263
San Diego Chicago Thu, Jan 8 - Tue, Jan 13 $252
Fort Lauderdale Chicago Tue, Feb 3 - Wed, Feb 4 $177
Las Vegas Chicago Wed, Jan 7 - Sat, Jan 10 $199
Guadalajara Chicago Wed, Dec 31 - Thu, Jan 15 $411
Tampa Chicago Fri, Jan 16 - Wed, Jan 21 $119
Houston Chicago Thu, Jan 8 - Tue, Jan 13 $135
Baltimore Chicago Mon, Jan 5 - Mon, Jan 12 $177
Honolulu Chicago Tue, Dec 30 - Fri, Jan 2 $839
Orange County Chicago Tue, Jan 13 - Mon, Jan 26 $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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