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

Congress Plaza Hotel at Grant Park

Historic hotel on Michigan Avenue by Grant ParkGuests at the Congress Plaza Hotel at Grant Park hotel enjoy value prices and a convenient location across from Grant Park, Buckingham Fountain, Millennium Park, the Art Institute and Lake Michigan. Designed to accommodate large groups, the 850-room hotel has hosted legions of tourists, conventioneers and even the nation’s presidents since the World’s Columbian Exposition in 1893. Its presence among Chicago architecture is unmistakable: Just look for the oversized sign in all red caps. Highlights Spectacular views of Grant Park, Buckingham Fountain, Lake MichiganTwo restaurants and a lounge on site Wireless Internet in the lobby RoomsRooms at the Congress Plaza Hotel at Grant Park hotel favor space over flash. Find rooms and spacious suites of various sizes -- many with lakefront views -- as well as high ceilings and parlor seating. Complimentary wired and wireless Internet access are also available. FeaturesThe Congress Plaza Hotel at Grant Park serves as a top reception site for weddings, conferences and other formal events. The lobby with its massive mosaic-tiled ceiling inspires awe in both guests and architecture fans. More than 50,000 square feet of meeting space, including the gorgeous Gold Room with its gold-leaf covered walls and ceilings, lend opulence to any occasion.Diners visit the Gazebo Restaurant, a casual restaurant serving breakfast and lunch, or Rafael's Steakhouse, a more intimate dinner venue. Cocktails and pub fare are available in the lounge.Other property amenities include a barbershop, game room and fitness center. Transportation O’Hare International Airport (16.1 mi/25.8 km) Midway Airport (8.9 mi/14.4 km) Blue Line (LaSalle) (0.9 mi/1.5 km) Orange Line (Library) (0.3 mi/0.5 km) McCormick Place Convention Center (1.7 mi/2.7 km) Nearby attractions Grant Park (across the street) State Street (0.1 mi/0.2 km)Buckingham Fountain (0.3 mi/0.5 km)The Art Institute of Chicago (0.4 mi/0.6 km)Millennium Park (0.5 mi/0.9 km)Soldier Field (1 mi/1.6 km)The Magnificent Mile (1.3 mi/2.1 km) Policies and fees Valet Parking $44.00 for overnight parkingSelf-Parking $39.00 for overnight parking
Value Save 20% on your stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $95

Raffaello Hotel

Boutique luxury in the heart of the Gold Coast In Chicago, the rule for downtown real estate is the closer to Lake Michigan, the more posh the address. Enter the Raffaello Hotel, a four-star hotel just steps from the lake and Magnificent Mile with a Michelin-rated chef and executive suites. Blending old-world aesthetics with modern conveniences, the hotel manages luxury and intimacy while being near the downtown hub. Stepping into the vintage building just off the tourist drag, guests are more likely to feel like Gold Coast residents than tourists. Raffaello Hotel offers Drumbar, a rooftop speakeasy-style inside lounge and outdoor garden terrace, found in the 18th floor. Highlights Walk to the Magnificent MileNext to the John Hancock CenterRooftop sundeckUpscale Italian fare at PelagoSanctuary fitness center with Precor fitness equipment RoomsStaying in this vintage building poses several advantages. The Raffaello Hotel offers rooms with high ceilings and architectural details for a unique, high-class vintage stay. Butterscotch-hued bedding and drapes match the walls, while high ceilings --painted stark white--stun with their beam construction. All rooms feature rainfall showerheads, GUYandGIRL amenities, 32-inch LCD TV, iHome and iPod players and 340-count linens. Rooms, which come in king, double double and suite versions are hard-wire and Wi-Fi enabled. Features Any Chicagoan will encourage a newcomer to put dining and an architectural experience on the itinerary. At the Raffaello Hotel, both needs are satisfied thanks to Pelago, the upscale Italian seafood restaurant and the rooftop garden, which is open from late spring to late fall. From the sundeck, guests can take in glorious views of the skyline, including Navy Pier and the next door neighbor: the John Hancock Center. Transportation O'Hare International Airport (18 miles)Midway Airport (12 miles)Closest train stops: Blue Line (Chicago to O'Hare) and Orange Line (Roosevelt to Midway)McCormick Place Convention Center (11 minutes) Attractions John Hancock CenterAmerican Girl PlaceMagnificent MileOak Street ShoppingOak Street BeachNavy PierLake Michigan Policies and fees Wi-Fi access is complimentary. Standard Wi-Fi access fee with 3 MBPS that can connect up to three devices per day is $4.99 USD while Premium Wi-Fi access fee with 5 MBPS that can connect up to three devices per day is $9.99 USD.The hotel charges a $10 USD handling fee per storing package.The hotel charges a $25 USD for each additional guest.Photo identification and credit card are required at check in for incidental charges. If you do not provide a credit card, a cash security deposit in the amount of $1,000 is required.The hotel charges $61 USD for valet parking and $34 USD for self-parking.
Value Stay 3 nights, Save 35%
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $119

The Talbott Hotel

This Property is 100% Non-Smoking. The Talbott Hotel in the heart of the Gold Coast offers spacious rooms with complimentary amenities including wireless internet and access to Equinox Fitness. Located steps from Chicago's Magnificent Mile and Rush Street, the heart of Chicago's night life. Voted as an Orbitz Best of the Best hotel. The Talbott Hotel is recognized as a leader in both leisure and business travel. It offers impeccable service with its concierge staff, all Les Clefs d'Or members, to assist with your evening plans or sightseeing. After a day of excitement, relax and unwind in your oversized guest room. The elegant marble bath stocked with fine Molton Brown Bath and Spa products in your guest room or your suite. Dry off with your luxurious Frette bath linens, and sink into a terrycloth robe while enjoying a program on your 42" LCD flat screen television with 30 High Definition Channels. Nightly turndown service; we will refresh your room, turn down your bed and leave you with delectable chocolate. You will be fully rested and ready to start another day of exploration after sleeping in one of our plush pillow top beds with luxurious linens, down pillows and comforter. Another day of relaxation and luxury awaits you tomorrow Imagine the rest. * Certified "Green Seal" Hotel. * 100% of the hotels electrical carbon footprint is offset by Wind Energy. * Four Diamond Rated by AAA. * Guests must be at least 21 years of age to check in. Valet Parking Rates 1 hour or less - staying at $22.00 1 - 3 hours - staying at $26.00 3 - 8 hours - increasing from $32.00 to $34.00 8 - 24 hours - increasing from $51.00 to $58.00 Little Market Brasserie - increasing from $13.00 to $14.00 Self Park - increasing from $36.00 to $40.00 with Validation otherwise $44.00 without. A $20 fee per person, per night will apply to all reservations where there are more than 2 people staying in a room and will be charged directly by the hotel. Extra beds are also available upon request for a fee of $24/night. See Front Desk for more information.
Value Stay tonight and save!
Flight + Hotel
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Hotel only
Nightly rates from $132

Monaco Chicago, a Kimpton Hotel

Sleep with the goldfishes at Chicago hotel with comfort food restaurant Overlook the river from many of the inspired rooms at the Monaco Chicago, a Kimpton Hotel. Layers of colorful eye candy in retro-modern style and funky patterns fill this hotel with an urban kick and attentive service. Just steps from luxurious shopping of Michigan Avenue, catch the scent of American regional dishes wafting from on-site South Water Kitchen. Pour a cup of coffee or tea each morning before walking to top Chicago sites. Meet fellow guests over a bold red or crisp white at the evening wine hour at the Monaco Chicago, a Kimpton Hotel. Highlights On-site diningComplementary morning coffee in the lobby, plus an evening hosted wine receptionUp-to-date 24/7 fitness center and in-room spa treatmentsPet-friendly rooms or request an in-room goldfishFree shoeshine and morning newspaper Rooms Slightly exotic yet sophisticated, the 191 spacious rooms and suites at the Monaco Chicago, a Kimpton Hotel add unexpected touches to appeal to guests' creative sides. All rooms feel upgraded with animal-print bathrobes, plush window seats, Frette linens, Aveda bath amenities, flat-screen TVs, gourmet stocked honor bars and a 24-hour room service menu. Some boast river views to boot. Those traveling with pets find food and water bowls plus an in-room dog bed at the Monaco Chicago, a Kimpton Hotel. Pet-less guests request a staff-attended-to goldfish for extra in-room company. High-speed wireless Internet access is available throughout the hotel (fees apply). Features For downtown convenience, use the valet parking with in-and-out privileges (fees apply) at the Monaco Chicago, a Kimpton Hotel. Business folks appreciate a complimentary shoeshine and daily newspaper upon request, while fitness nuts hit the fitness center or jog along the nearby Chicago Riverwalk. Pick up a pass to LA Fitness club one block away to work with personal trainers or take a swim (fees apply). Transportation Midway International Airport (12.9 mi/20.7 km)O'Hare International Airport (18.3 mi/29.5 km)Several subway stations (0.1 mi/0.2 km) Attractions Millennium Park (0.5 mi/0.7 km)Magnificent Mile (0.5 mi/0.7 km)Art Institute of Chicago (0.5 mi/0.8 km)Willis Tower (1.1 mi/1.7 km)Navy Pier (1.3 mi/2 km)Field Museum of Natural History (1.9 mi/3 km)Lincoln Park Zoo (2.5 mi/4 km)McCormick Place (2.7 mi/4.3 km) Business High-speed wireless Internet access (fees apply)24-hour business center with Mac and PC computers and printerFlexible meeting rooms accommodate up to 300 people
Value Save 10% on your stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $143

Millennium Knickerbocker Hotel

Chicago hotel on Magnificent Mile with hip martini bar and restaurantIn 1927, notable architects Rissman & Hirschfield, responsible for many highlights on the Chicago skyline, finished a 14-story, gothic-inspired hotel that is now known as the Millennium Knickerbocker Hotel. Newly-redesigned guest rooms with spa-style bathrooms entice guests to stay at this classic gateway to the Magnificent Mile. Historical architecture charms while the prime location of the Millennium Knickerbocker Hotel allows for a short walk to business meetings in the Loop, famed Chicago attractions and Michigan Avenue shopping. Highlights M Bar serves more than 50 martinis and wines, plus light fare with live entertainmentOn-site restaurantHistoric Magnificent Mile hotel with newly-designed rooms Saturday night Dinner Detective Mystery Show (fees apply) RoomsAfter a complete redesign, the 306 guest rooms and suites at the Millennium Knickerbocker Hotel show off their new look and enhanced comfort with Sealy pillow-top bedding, Frette linens, down comforters and plush pillows. A quiet, toned down neutral scheme receives a punch of cranberry for style. Slip into the terrycloth robe and slippers, pull the blackout shades and raid the stocked mini-bar or unwind in front of the 40-inch flat-screen TV at the Millennium Knickerbocker Hotel. Bathrooms gleam with spa-inspired design and a rain shower. Connect to high-speed wireless Internet at will (fees apply). Features Guests start the day at NiX restaurant, a white-tablecloth bistro that serves breakfast and lunch at the Millennium Knickerbocker Hotel. After dark, pop into M Bar for a signature martini and live music. Nearly every Saturday night, the Millennium Knickerbocker Hotel hosts the Dinner Detective Murder Mystery, a top Chicago murder mystery event and dinner show. The hotel also offers in-room spa treatments, a palatial ballroom with gold domed ceiling and valet parking with in-and-out privileges (fees apply). Transportation Midway International Airport (13.8 mi/22.3 km)O'Hare International Airport (18.4 mi/29.6 km)Several subway stations (0.1 mi/0.2 km) Attractions Magnificent Mile (across the street)Millennium Park (1.5 mi/2.4 km)Art Institute of Chicago (1.6 mi/2.5 km)Navy Pier (2 mi/3 km)Willis Tower (2.3 mi/3.6 km)Lincoln Park Zoo (2.4 mi/3.9 km)Field Museum of Natural History (4.2 mi/6.7 km)Wrigley Field (4.3 mi/7 km)McCormick Place (5.9 mi/9.5 km) Business High-speed wireless Internet access throughout the hotel (fees apply)24-hour business center18,500 square feet across 16 meeting rooms accommodate up to 750 people
Value Save 15% on your stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $129
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Sat, May 31 - Tue, Jun 3 $208
Los Angeles Chicago Sat, May 10 - Tue, May 13 $268
Washington DC Chicago Sat, May 10 - Wed, May 14 $262
San Francisco Chicago Wed, May 14 - Sat, May 31 $278
Newark Chicago Tue, Jun 17 - Wed, Jun 25 $224
Atlanta Chicago Mon, May 26 - Tue, May 27 $242
Seattle Chicago Sat, May 10 - Sat, May 31 $313
Boston Chicago Tue, Jun 10 - Tue, Jun 17 $158
Dallas Chicago Wed, Jun 4 - Tue, Jun 10 $168
Denver Chicago Wed, May 14 - Thu, May 15 $164
Phoenix Chicago Wed, May 14 - Fri, May 16 $257
Orlando Chicago Tue, Jun 10 - Wed, Jun 25 $204
San Juan Chicago Thu, May 1 - Tue, May 13 $279
Mexico City Chicago Wed, May 21 - Sun, May 25 $515
Philadelphia Chicago Wed, Jun 18 - Tue, Jun 24 $320
San Diego Chicago Tue, Jun 10 - Tue, Jun 17 $288
Fort Lauderdale Chicago Tue, May 6 - Wed, May 7 $280
Las Vegas Chicago Tue, May 13 - Tue, May 20 $268
Guadalajara Chicago Wed, May 7 - Sun, May 18 $430
Tampa Chicago Mon, Jun 16 - Sat, Jun 21 $253
Houston Chicago Wed, May 28 - Sat, May 31 $207
Baltimore Chicago Wed, May 28 - Tue, Jun 3 $148
Honolulu Chicago Tue, May 6 - Tue, May 13 $840
Orange County Chicago Sat, May 17 - Sat, May 24 $302
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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.

Your trip

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