Cheap Chicago Vacations


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

Virgin Hotels Chicago

4 stars
Not yet reviewed
Deluxe hotel in downtown Chicago with five food and beverage venuesDiscerning travelers looking to explore bustling Chicago find strategic base at the upscale accommodations of Virgin Hotels Chicago. This centrally located hotel places holidaymakers within convenient distance to the business district and go-to points of interests including Millennium Park, Chicago Theater and the lively Navy Pier. For on-site dining options, the property features five restaurant and lounge experiences, including Miss Ricky's, a reinvented American diner, 203, a Euro-style coffee and wine bar and The Commons Club, a lounge and restaurant. Visitors can also unwind with cocktails at in-house The Rooftop Bar, offering scenic city vista. Virgin Hotels Chicago offers three flexible event venues that can host corporate and social gatherings of up to 108 people. After attending to business matters, guests can take a break by working out at the rooftop gym on site. The property also provides complimentary Wi-Fi access for added convenience. 3 Reasons To StayTwo-chamber spacesFree Wi-Fi accessMeeting venues for up to 108 people Virgin Hotels Chicago RoomsVirgin Hotels Chicago boasts modern two-chamber rooms and suites featuring separate bedroom and dressing area with closet and bathroom. All units are outfitted with sliding privacy doors, entertainment system and mini bar. Room service is also provided. Things To Do Chicago Theater (0.09 mi/0.14 km)Oriental Theater (0.2 mi/ 0.3 km)Goodman Theater (0.2 mi/ 0.3 km)Millennium Park (0.3 mi/ 0.5 km)Buckingham Fountain (0.8 mi/1.3 km)Museum of Contemporary Art, Chicago (0.8 mi/1.3 km)Navy Pier (1.0 mi/1.6 km)Shedd Aquarium (1.4 mi/2.3 km)The Field Museum (1.4 mi/2.3 km)Lincoln Park Zoo (2.4 mi/3.8 km)Wrigley Field (4.6 mi/7.4 km)
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $195

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
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Hotel only
Nightly rates from $80

The Talbott Hotel

4 stars
4.6 / 5 1256 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
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Nightly rates from $124

Wyndham Grand Chicago Riverfront

3 stars
4.2 / 5 257 reviews
Boutique chic near the Magnificent Mile in ChicagoWyndham Grand Chicago Riverfront is a boutique hotel located in the heart of downtown Chicago. The hotel's unrivalled location is in the center of all Chicago has to offer, within walking distance of Navy Pier, the Magnificent Mile, Millennium Park, the theatre district and the Loop. The 39-story hotel features chic interior with a bright lobby and oversized, relaxing guest rooms. Wyndham Grand Chicago Riverfront offers an complimentary 24 fitness center, complimentary 24 hour business center, in addition to complimentary wireless internet for all guests. Minimum check-in age is 21. Highlights Rooms with views of the Chicago River, Trump Tower and Merchandise Mart Near upscale department stores and luxury boutiques on the Magnificent Mile 24-hour business center and free Wi-FiHoyt's Chicago Restaurant on site RoomsExpect spacious rooms with gorgeous city and river views at Wyndham Grand Chicago Riverfront. Neutral colors, suede headboards and flowing drapes provide a relaxing environment. Extras like Keurig coffee makers, flat-screen TVs and iPod docking stations are standard. Enjoy free high-speed wireless Internet access. DiningThe first floor restaurant, Hoyt's Chicago, reflects modern tavern fare while focusing on a true Chicago neighborhood dining experience. At Wyndham Grand Chicago Riverfront, diners can savour the seasonal, market fresh and healthy offerings with a creative twist while taking in views of the iconic Chicago River through the floor-to-ceiling windows.Hoyt's serves breakfast, lunch, and dinner and also offer full bar service Transportation O’Hare International Airport (15.6 mi/25.1 km) Chicago Midway Airport (9.5 mi/15.3 km) Blue Line (Clark/Lake) (1.7 mi/2.7 km) Orange Line (State/Lake) (0.2 mi/0.3 km) McCormick Place Convention Center (5.1 mi/8.1 km) Attractions Chicago River (0.1 mi/0.1 km)Jewelers Row (0.4 mi/0.6 km) Millennium Park (0.4 mi/0.6 km) Theater district (0.4 mi/0.7 km) The Magnificent Mile (0.5 mi/0.7 km) Lake Michigan (0.5 mi/0.8 km) The Art Institute of Chicago (0.5 mi/0.8 km) Grant Park (0.8 mi/1.2 km) Business 24-hour business center with high-speed Internet access Six meeting rooms and seven boardrooms featuring a private sleeping room Catering for meetings and events Policies and fees The hotel no longer accepts cash deposit. Credit card is required at check-in. Guests can still pay cash for bill at the end of stay.Overnight valet parking rate is $55 USD starting 01 April.Dogs under 50 lbs are welcome with a $100 non refundable deposit.The minimum check-in age for Wyndham Grand Chicago Riverfront is 21 years of age.
Value Save 10% on your stay
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Nightly rates from $119

The Silversmith Hotel Chicago

3 stars
4.2 / 5 237 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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Hotel only
Nightly rates from $97
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Sat, Mar 7 - Tue, Mar 10 $87
Los Angeles Chicago Thu, Mar 5 - Wed, Mar 11 $237
Washington DC Chicago Wed, Feb 11 - Sat, Feb 14 $98
San Francisco Chicago Tue, Feb 10 - Wed, Feb 18 $246
Newark Chicago Tue, Mar 10 - Tue, Mar 17 $177
Atlanta Chicago Sat, Feb 21 - Tue, Feb 24 $98
Seattle Chicago Tue, Mar 3 - Wed, Mar 11 $288
Boston Chicago Wed, Feb 4 - Thu, Feb 5 $140
Dallas Chicago Tue, Feb 17 - Wed, Feb 18 $107
Denver Chicago Wed, Feb 11 - Tue, Feb 17 $97
Phoenix Chicago Tue, Feb 10 - Tue, Feb 24 $137
Orlando Chicago Sat, Feb 14 - Tue, Feb 24 $160
San Juan Chicago Tue, Feb 10 - Tue, Feb 17 $332
Mexico City Chicago Thu, Mar 5 - Thu, Mar 12 $336
Philadelphia Chicago Wed, Mar 25 - Tue, Mar 31 $98
San Diego Chicago Tue, Feb 10 - Tue, Feb 17 $298
Fort Lauderdale Chicago Sat, Feb 21 - Sat, Feb 28 $177
Las Vegas Chicago Tue, Mar 10 - Tue, Mar 17 $137
Guadalajara Chicago Tue, Feb 24 - Sat, Mar 14 $386
Tampa Chicago Wed, Feb 18 - Tue, Feb 24 $127
Houston Chicago Wed, Feb 18 - Mon, Feb 23 $115
Baltimore Chicago Wed, Feb 11 - Wed, Feb 18 $117
Honolulu Chicago Fri, Feb 6 - Sun, Feb 15 $715
Orange County Chicago Tue, Mar 3 - Tue, Mar 10 $287
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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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