How to Find Cheap Flights & Accommodations in Chicago, Illinois, United States

All Topics about Chicago All Cities in United States

1. Skyscanner

Comparing flights from hundreds of airlines and travel agents to get the best deal for your Chicago trip.

Price Comparison: Offers price comparison across multiple sites to ensure you're getting the cheapest flight.
Flexible Dates: Lets you check prices for different dates and choose the most affordable one.
Flight Alerts: Allows you to set fare alerts for your desired route, getting notified when fares drop.

Searching for the cheapest flights and hotels in Chicago on a single platform.

Travel Hacking Tools: Provides tools to find hidden city flights, rental cars, vacation rentals, and activities.
Price Prediction: Predicts price trends based on historical data to help you decide when to book your flight.
Hacker Fares: Shows you 'hacker fares,' which can result in significant savings when booking flights.

Booking flights, hotels, and vacation packages to Chicago with discounts and savings.

Discounts: Offers exclusive deals and discounts on flights and hotels not found elsewhere.
Flexible Booking: Allows you to cancel or change your travel plans if necessary, with minimal fees.
Price Drop Protection: If the price drops after booking, Orbitz will refund the difference.

Find deals on flights, hotels, and rental cars for your Chicago trip on Expedia.

Package Deals: Offers package deals that bundle flights, hotels, and rental cars together, saving you money.
Loyalty Program: Members of the Expedia Rewards program can earn points towards future travel rewards.
Price Match Guarantee: If you find a lower price elsewhere, Expedia will match it and give you $50 back.

Find cheap flights, hotels, and car rentals in Chicago by booking 'hot rates' on Hotwire.

Hot Rates: Books flights and hotels at discounted rates without knowing the specific airline or hotel.
Express Deals: Offers last-minute deals on flights, hotels, and car rentals with up to 60% off.
Gift Cards: Buying Hotwire gift cards at a discount can lead to significant savings on travel.

Book cheap flights, hotels, and rental cars in Chicago with Priceline's 'Name Your Own Price' feature.

Name Your Own Price: Allows you to set your own price for flights, hotels, and car rentals.
Exclusive Hotels: Offers exclusive deals on popular hotels in Chicago.
Express Deals: Provides last-minute deals on flights, hotels, and car rentals with up to 60% off.

Find cheap flights, hotels, and vacation packages in Chicago on Travelocity.

Farewatcher Alerts: Allows you to set fare alerts for your desired route and get notified when prices drop.
Deal Finder: Finds deals on flights, hotels, and car rentals, even if they're from smaller sites or airlines.
Price Match Guarantee: If you find the same flight for less elsewhere, Travelocity will match it and give you $50 back.

Rent unique and affordable accommodations in Chicago from locals on Airbnb.

Experience Local Life: Stay in a local's home to experience the city like a resident.
Affordable Prices: Offers budget-friendly options for longer stays or large groups.
Variety of Choices: Provides a wide range of accommodations, from entire homes to private rooms.

Book affordable hostels in Chicago and meet fellow travelers.

Social Atmosphere: Hostels offer a social atmosphere, making it easier to meet other travelers.
Affordable Prices: Hostels are generally cheaper than hotels or Airbnb options.
Convenient Locations: Many hostels are centrally located, making it easy to explore the city.

Find last-minute deals on hotels in Chicago with Hotel Tonight.

Last-Minute Deals: Offers deep discounts on last-minute hotel bookings.
User Experience: Easy-to-use app makes it quick and simple to book a room.
Exclusive Rates: Offers exclusive rates that can't be found on other booking sites.

Find affordable hostels and accommodations in Chicago with the CHA.

Affordable Prices: Hostels are generally cheaper than hotels or Airbnb options.
Support Local Organizations: By staying at CHA-affiliated hostels, you're supporting a local organization.
Variety of Choices: CHA hosts a range of hostels offering various amenities and locations in the city.

Discover charming bed & breakfasts in Chicago with CBBBA.

Personal Experience: Staying at a B&B provides a more personalized and memorable experience.
Affordable Prices: Many Chicago B&Bs offer affordable rates, especially for multi-night stays.
Unique Accommodations: Each B&B offers a unique experience and character, providing a diverse selection to choose from.

Book accommodations in Chicago directly with the hotel or hostel for the best deals.

Direct Savings: Booking directly can lead to additional savings and perks, such as free upgrades.
Support Local Businesses: By booking direct, you're supporting local businesses in Chicago.
Personalized Service: Booking directly allows for a more personalized experience and service.

Find deals on travel packages, including flights, hotels, and activities in Chicago on Groupon.

Travel Deals: Offers a wide range of travel deals, including flights, hotels, and activities.
Discounted Prices: Provides discounts on packages that can't be found elsewhere.
Flexible Dates: Allows you to choose from multiple dates and times for your Chicago trip.

Find deals on travel, including hotels, flights, and activities in Chicago on Travelzoo.

Travel Deals: Offers a wide range of travel deals, including flights, hotels, and activities.
Discounted Prices: Provides discounts on packages that can't be found elsewhere.
Flexible Dates: Allows you to choose from multiple dates and times for your Chicago trip.